


Dan the Personal Assistant

by blissedoutphil



Category: Phandom/The Fantastic Foursome (YouTube RPF)
Genre: Anal Fingering, Angst, Blow Jobs, Butt Plugs, Cock Warming, Deepthroating, Dom Phil Lester, Dom/sub, Face-Fucking, Fluff, Fluff and Angst, Hand Jobs, Humiliation, M/M, Office Blow Jobs, Office Sex, Paddling, Punishment, Smut, Spanking, Sub Dan Howell, Vibrators
Language: English
Status: In-Progress
Published: 2019-01-01
Updated: 2019-08-25
Packaged: 2019-10-02 06:04:32
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 7
Words: 24,305
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17258921
Author URL: https://archiveofourown.org/users/blissedoutphil/pseuds/blissedoutphil
Summary: Dan has to submit an application video to be an assistant for a company President, Mr. Lester. But what happens when he accidentally sends a wrong video?





	1. Chapter 1

**Author's Note:**

> Happy 2019! May this year bring shorter hiatuses from me (and d&p too lmao)
> 
> This was a prompt given to my tumblr!

Dan fiddled with the cufflink on his shirt. Nervous would be an understatement for how he was feeling at the moment. He absolutely  _cannot_  mess this up.

Sitting in the waiting area, Dan glanced over to see his competition. All the other applicants seemed way more suitable for the job. They looked poised, calm, confident. Ready to start the job immediately. Meanwhile his hair was still a curly mess, his cheap shirt crumpled. He wasn’t sure how he passed the first round of application if these people around him were what the company was looking for.

He’d arrived later than he was supposed to and missed his interview slot, so he was expected to be turned away immediately. But apparently the company President still wanted to meet him, so there he was, about to go for his first job interview in a year. He might finally be employed again. Properly employed, instead of working random odd jobs just to survive. He watched as the final applicant before him entered the room.

Dan gulped, running through common interview questions in his head. What are his strengths? Nothing. What are his weaknesses? Everything? Was his job submission video even good enough to be able to get into this round? He could barely remember what he said in the video. He must’ve bullshitted his way through it and now he has to go even further down the spiral of lies he’d created.

Hell, Dan could barely remember even submitting the video. All he knew was that he was drunk on the final day to submit it, and his phone reminder set off to yell at him to submit it while he was enjoying a lazy drunken jack off. Dan had quickly emailed his submission so he could go back to masturbating, but til this moment he hadn’t checked if his email was proper and formal enough. He didn’t care, he must’ve done it right since he was there now anyway.

He almost jumped out of his seat when the door opened. The applicant before him gave a polite nod, and he nodded back. 

 _Get yourself together, damn it_ , Dan thought,  _If you can bullshit your way this far, you can certainly do it in there_. He walked up to the door and knocked on it, mustering up as much confidence as he could.

He heard a faint  _Come in_ , and slowly opened the door to enter the room.

“Have a seat, Mr Howell,” The company President smiled at him.

“Th-thank you,” Dan stumbled and quickly sat down.

The boss didn’t look as intimidating as Dan had thought he would be. He wasn’t old, as he would expect an accountant with his own successful company to be. Perhaps in his mid-thirties, so just a little over ten years older than Dan. His smile was comforting, welcoming. And Dan couldn’t help but be transfixed by his striking blue eyes. Dan found himself relaxing into the seat. 

“So Mr Howell, first of all, congrats on passing the first round,” Mr Lester spoke, leaning back in his chair a little, “I quite enjoyed your video. You made it entertaining, unlike most submissions.”

Dan smiled, thanking him again.

“But I do feel like I still don’t know you well enough from the video itself. So maybe we can start this off with, why do you want this job?”

Dan cleared his throat a little. He was sure that he’d explained this part in his video, and he hadn’t prepared answers that were different to his video.

“Well, I did mention in the video that I think I’m suitable to be your assistant because I am meticulous. I, uh,” Dan paused, trying to come up with more half truths and recall what he’d mentioned in his video.

Mr Lester looked at him intently throughout his explanation, running his eyes up and down his face as if trying to memorise every little freckle and blemish. If it wasn’t an interview, Dan would’ve thought that Mr Lester was perhaps checking him out a little.

“Interesting,” Mr Lester offered after Dan finished speaking, “You explained that in your video? I must have missed that part then.”

Dan mentally slapped himself. The boss certainly did not sound like he bought his explanation.

“Yes I would definitely need my admin assistant to be meticulous, it’s probably the most important trait that they need to have in an accounting firm. Some applicants try out for this job when they’re the complete opposite of that,” Mr Lester shook his head and chuckled.

Dan didn’t know how to respond to that so he just chuckled uncomfortably back.

“I mean, I’ve received wrong formats of the video submission. Wrong versions. Many applicants coming to me crying and apologizing and asking me to accept a newer version. There’s no room for such mistakes in this company!”

Dan agreed, although now he was starting to get intimidated. He was slowly accepting the fact that he wouldn’t get the job, and he’d totally be fine with it. He was admittedly a careless person who could risk causing this man problems with his accounts, and he did not need that kind of trouble in his life, no matter how badly he needed the money.

“One person,” Mr Lester chuckled, a mischievous glint in his eye, “even sent me a porn video of himself!”

“What?” Dan laughed, feeling horrified on behalf of that poor applicant.

Mr Lester held eye contact with him, making Dan feel small but somehow he couldn’t look away.

“I know right? I don’t know if he was aware of it at all, because he still hasn’t gotten back to me about it. Do you think those type of people are meticulous?”

Dan shook his head no, unsure where this interview was heading. Was there a need to talk about other applicants like this?

Mr Lester was silent, and Dan bit on his lip. Was he supposed to elaborate on his answer or something?

“Yeah no, I don’t think meticulous is a word to describe that kind of person,” Dan voiced it out in case the boss wanted to hear it instead of just seeing him shake his head.

“Then why did you call yourself meticulous?” Mr Lester’s voice dropped low, deep and intimidating.

But Dan didn’t understand his question. His confusion must have been clear on his face as Mr Lester looked slightly amused. The boss silently turned his computer screen to Dan’s direction.

Mr Lester looked on in amusement as the expression on the boy in front of him changed from confusion to horror in a matter of seconds. The colour drained from his face and his mouth fell open as he sat frozen in his seat.

On the computer screen was Dan having a threesome. A threesome that he had had the day before the video submission deadline. A threesome that he’d watched while jacking off drunk before being interrupted by his phone reminding him to submit his video.

“Oh, my favourite part’s coming,” Mr Lester said very casually.

 _Fuck_. Dan wanted to die right there. This cannot be real. Perhaps if he pinched himself hard enough, he’d wake up from this nightmare. He wanted to leave immediately but his legs couldn’t even work.

Mr Lester’s favourite part of the video was apparently when Dan managed to ride two dicks at once. Dan in the video was moaning loud as he bounced on top of one man, another man flush against his back.

“I-I gotta-” Dan managed to utter as he shakily got up, tripping over his own feet at an attempt to rush out.

This  _cannot_  be happening. How had he managed to send that video instead? Dan wanted the ground to swallow him up.

“It’s a shame you gotta go because I was about to hire you!”

Dan froze for a second time. Was this man kidding? Wasn’t the humiliation enough already, now he gotta go even further in his convoluted way of teaching Dan a lesson on meticulousness?

“Was gonna give you a higher salary than the job you originally applied for, too.” 

“What do you mean?” Dan asked softly, daring himself to turn back to the boss.

“Sit back down and allow me to explain.”

Dan sighed. He wasn’t sure if he was able to face the man - the company’s fucking  _President -_ who watched him take two dicks up his ass ever again. But at the same time, his rent was overdue and he really needed the money.

He slowly sat back down but avoided eye contact, looking at his lap instead of the boss.

“I never expected to receive something like your video submission, but I am actually impressed by it, so I’m offering you to be my assistant. Not for admin though.  _Personal_  assistant, if you know what I mean,” Mr Lester leaned forward, looking dead serious.

Dan couldn’t believe what he was hearing. Was he being offered a job as a personal whore? Did this man really think Dan had no dignity in him?

“Like your personal whore or something?” Dan couldn’t help but sound offended.

“Well it does sound bad if you put it like that,” Phil chuckled sheepishly, “Let’s stick to personal assistant, yeah? I can give you a 5 figure salary for it.”

With the mention of money, Dan realised that he really did have zero dignity left.

* * *

Mr Lester took hiring him very seriously. Dan was given a contract and 3 days to read it all and sign it. He’d actually already accepted the job immediately, but Mr Lester really wanted to make sure that Dan knew what he was getting into even though he was excited that Dan was willing to do it.

 _Phil’s personal assistant_ , Dan read the top of the contract. He wondered if he would be Phil’s first ever PA, or if Phil got tired of his last one and Dan was lucky enough to accidentally submit his porn. Or if he had more PAs that Dan would be having threesomes with one day.

Reading the contract gave Dan the realisation that Phil was one kinky man. He wasn’t complaining though, he loved most of the kinks listed, and for 10 grand, he was willing to try out anything. Phil being hot was an added bonus, and Dan was honestly worried about how his first thought upon reading the kinks was that he wouldn’t mind doing it for Phil even if he wasn’t getting paid.

Dan returned to the office the next day with the signed contract, even though Phil kept asking him to give a proper think if he really wanted to do it.

But Dan really did want to do it. If he’s good at anything at all, it was sex. He would definitely enjoy this job more than some boring admin job. And why would he turn down getting paid to do what he’s good at, plus with the most attractive man he’s ever met?

Phil was more than delighted when he was finally assured that Dan was serious about accepting the offer. He sent Dan home with some instructions to start his first day of work proper the next day.

* * *

Dan had to come in an hour earlier than everyone else in the office everyday, in case Phil wanted a quickie before starting his day. Dan wondered why a man as rich and handsome as Phil doesn’t have a partner. But he didn’t dwell on it, he’s lucky that Phil was single because if not he might not have this job.

For once, Dan actually arrived on time. He was to go straight to Phil’s room, and he’d been given the key. He locked himself in the room, not sure if the rest of the office was meant to know his presence. Was he going to be Phil’s little secret? Or was Phil going to share him with other bored colleagues? He felt a tingle of excitement thinking about it.

Dan walked around the room, taking in the sight of his new workplace which he didn’t get to do much of during his other visits. Phil’s desk was huge at one end of the room. The walls of the room were all glass, overlooking the city. Dan gulped as he looked at the view, remembering that exhibition kink was listed in his contract. 

There were three little couches and a small coffee table in the centre of the room, and at the end of the room was a little pantry. There was even a connecting bathroom, which Dan was grateful for because he certainly did not want to have to leave the room and face other people in the office if he needed to pee.

Dan was standing in the mini pantry contemplating whether it was acceptable of him to make a coffee without permission on his first day of work when the door swung open.

He turned around in surprise, but relaxed when he saw Phil sauntering in.

“Good morning,” Dan said softly. He knew Phil was a nice man, but he can’t help still feeling a little intimidated by him.

“Good morning, Dan,” Phil smiled brightly at him, and Dan wondered how one can be so cheerful this early in the morning.

“Excited to start your new job?” Phil asked cheekily, smirking at Dan.

Dan blushed, but he couldn’t deny that he was excited, so he nodded shyly.

“Well then first things first, you need to be in proper attire. Your uniform, if you will,” Phil spoke as he busied himself to put away his bag and papers that he was carrying.

Dan looked on curiously, wondering what his uniform was. All blood rushed to his cheeks when Phil continued speaking.

“Strip.”

Dan looked at Phil wide eyed, he didn’t expect to be naked at all times. But the idea of it was very hot, and Dan gave a small nod before turning to head to the bathroom.

“Where are you going?” Phil asked, “Do it here.”

Dan’s cheeks were so warm he wondered if it was possible to blush this much. Phil was leaning against the desk, looking at him expectantly. Dan guessed that he should probably throw whatever little dignity he had left out of the glass wall, and he slowly started unbuttoning his shirt.

“Don’t worry, I won’t let anyone see you. Unless you want to. And except any unfortunate people spying into our window,” Phil chuckled, but his gaze was intense on Dan’s now naked top.

Dan awkwardly let his shirt fall to the floor, and his trousers followed suit. Lastly, he took off his underwear and awkwardly held it in front of his crotch. He glanced up shyly to see Phil smirking at him.

Phil walked up to him and took his underwear out of his hands.

“No need to hide anything,” Phil spoke as he circled Dan, observing his boy.

“Good to see that you’ve followed my instructions,” Phil commented, taking note of how well shaven his assistant’s body was.

When Phil seemed satisfied with what he saw, he went back to lean against his desk again.

“This is how I expect to see you every morning, understand?”

“Yes, Sir,” Dan replied, feeling like it was only appropriate to address his boss as such.

Phil smiled, seemingly approving of being called Sir. He instructed Dan to keep his clothes in a drawer under the coffee table, and Dan hurriedly did so before standing awkwardly in front of his boss again.

Phil was now sat behind his desk, and Dan felt so exposed and vulnerable. He would be lying if he said it wasn’t turning him on. He willed himself not to get a boner this early in his job, it’d be embarrassing.

“Well we’ve still got a bit of time before the office opens. How’s about you show me how qualified you are for this job?” Phil said suggestively, rolling his chair back a bit.

Dan walked over and knelt between Phil’s legs, already guessing where this was going. He stared up at Phil innocently, awaiting instructions.

“Good boy,” Phil breathed, and nodded to give Dan permission to continue.

Dan slowly unzipped Phil’s pants. He’d done this many times in his life, and judging from all his random hookups, he was good at it. But he suddenly felt too aware of all his actions, felt like he really needed to do his best. Perhaps it was because he was getting paid for it this time and he did not want Phil to think he’s wasting money on someone who can’t even give a proper blowjob.

He gently tucked Phil out of his underwear, licking his lips when he saw that Phil was already half hard. He looked back up at Phil for approval. He wanted nothing more than to suck on Phil immediately. Maybe he  _is_  a cockslut, and what about it? But he thought that it was only right to let Phil take the lead, so he waited.

Phil gently threaded his hand through Dan’s curls and slowly guided his head to his cock, encouraging him with a smile. He’d watched Dan’s video more times than he’d like to admit, and ever since he saw Dan giving the two other men blowjobs, he couldn’t wait to get that pretty mouth around his own cock.

Dan happily went down, suckling on the tip. He hummed when Phil stroked his hair, loving the gentle touches. He tentatively brought his hand up and slowly wrapped it around the length that wasn’t in his mouth. Encouraged by a breathy moan by Phil, he started to suck further down.

Dan began bobbing his head, hollowing his cheeks and licking the underside of Phil’s shaft. He held the base of Phil’s cock as he sucked. Dan had given plenty of blowjobs before, but he probably only ever encountered someone as big as Phil once or twice. He tried his best to go as far down as he could, but he couldn’t fit all of Phil in his mouth.

To compensate for the lack of deepthroating abilities, Dan fondled Phil’s balls and stroked the parts he couldn’t fit in his mouth. He started to worry that Phil might find him disappointing for not being able to suck all of him in. He even wondered if he was going to get fired.

But Phil was enjoying all of it, moaning every time Dan moved up and licked his slit before going back down.

“You’re really good at this, boy,” Phil complimented, and Dan almost keened at the praise.

All of Dan’s worries disappeared upon hearing his boss praise him, and feeling his hand tangle in his hair. Dan hummed gratefully. Phil could easily push his head down to force him to take all of him in, but he liked how instead of that, Phil was being really tender with him. Perhaps this job was going to be the easiest and most fun he’d ever have.

After a while, Dan went off of Phil completely for some air, lips smacking with a pop sound. He looked up at Phil with doe eyes as he stroked him. The sight of his boss staring down at him through half lidded eyes and panting through his slightly open mouth was perhaps the most beautiful sight Dan had ever seen.

Dan gave kitten licks to Phil’s tip, all the way down to his crotch and back up again before going to suck on him properly again. Phil was throbbing and heavy against Dan’s tongue, and he sucked harder to help Phil reach his orgasm faster.

Phil moaned at the sight below him.  _The boy’s a natural_ , he thought. He was so glad that Dan had accepted the job offer, and at the moment he felt like the luckiest person in the world to have come across Dan.

He felt his orgasm approaching, but resisted the urge to fuck into the boy’s mouth. He wanted to go slow on their first day, treat him gently. Once Dan got used to this new job, he’d then gradually go harder and push his limits.

So Phil just tugged on Dan’s hair lightly and muttered a warning that he was close. Dan hummed around him, the vibrations sending shivers down his spine.

Dan could taste the salty precum as he moved faster down Phil’s cock. He swallowed around him a couple of times, earning groans from Phil.

“Gonna come, boy,” Phil warned, voice gravelly.

That signalled Dan to suck harder as one hand massaged Phil’s balls while the other stroked the base of Phil’s cock.

With a tug of Dan’s hair and a loud moan, Phil came down Dan’s throat. Dan swallowed it all, breathing harshly through his nose. He continued sucking on Phil until he couldn’t feel any more cum spurt down his mouth.

Dan only got off of Phil when Phil’s grip on his hair loosened. A string of spit and cum connected Phil’s tip to his reddened bottom lip, and Phil chuckled fondly at the sight.

‘i’m so glad I hired you,” Phil slurred, and Dan smiled shyly.

Dan had gone hard from giving the blowjob, but he barely noticed his own need to come until now. He wasn’t sure if asking to return the favour was a good idea, or if he was even allowed to touch himself. His contract did state that he was only allowed to do things when given permission, so he just sat on his heels with his palms flat on his thighs.

“I promise I’ll try to do better next time, you’re just so. Big,” Dan admitted softly, cheeks turning pink.

“Oh I definitely expect you to get better with time, but don’t worry because I’ll make sure you’ll have enough practice,” Phil smirked, “but you did really good for your first time, you were more  _meticulous_  than I expected.”

Dan rolled his eyes fondly at Phil’s praise at the end.

“Well, I better get started on my work. That was a good start to the day,” Phil ruffled Dan’s hair as he spoke.

“Uh,” Dan tried to articulate his need to come by pointing to his own hard on.

Phil chuckled down at him, “You’re getting paid to get  _me_  off, not yourself.”

And just like that his intimidating boss was back, Dan thought, and he regretted even trying to ask him for help.

“No touching yourself, got it? I’ll decide when you’ve earned it.”

Dan gulped, “Yes, Sir.”

Phil laughed a little, “Aww don’t look so worried. You’ve definitely been good enough so far to earn yourself an orgasm, but I’m afraid I don’t have time to help you out right now. Perhaps during lunch.”

Dan hoped he’d be able to control himself that long. Perhaps this job wasn’t going to be as easy as he thought earlier.

“You’re free to do whatever in here when you’re not needed. Hide in the bathroom if someone’s about to enter, or not if you don’t care for other people seeing you naked.”

* * *

Dan ended up spending his time sitting on the rug near Phil’s desk and dozing off. He was still feeling a little conscious about being fully naked in front of his boss, so he mostly sat in front of the desk where Phil could barely see his crotch.

Phil was too busy to even make small talk, but Dan didn’t mind. He enjoyed the comfortable silence that was only broken by Phil typing on the keyboard.

His boner died down soon enough, but he spent lunch receiving the best handjob he’d ever gotten in his life. He was embarrassed to have came all over his boss’s hand, but Phil merely chuckled and called him cute.

“It’s alright, boy, there’s nothing to be embarrassed about. You’ll get used to all this soon enough,” Phil had reassured him.

The rest of the day went by fairly quickly and Dan only had to hide in the bathroom once. Before he knew it, it was time to get dressed and head home.

Dan was certain that he was going to enjoy his new job. He couldn’t wait for the next day already. He can’t believe his fuck up and not being meticulous enough actually paid off.

**Notes for the Chapter:**

> yes I know I still have incomplete fics from last year but what do yall think about turning this into a series too? lmao let me know if I should continue it!  
> (tho I can't promise that updates will be frequent!)


	2. Chapter 2

**Notes for the Chapter:**

> Let's pretend I didn't just change the title of this fic......

The next day, Phil walked into his office to see his personal assistant already naked, awkwardly sat on the rug in front of his desk. He smiled a little, liking how the boy was naturally submissive without him even instructing. He still seemed nervous, and Phil hoped that he would get used to his new job sooner. He’d try his best to make his boy comfortable, it’s no fun playing with someone who was hesitant anyway.

“Good morning, Daniel,” Phil spoke up as he set his bag down.

Something about the way Phil said his full name out sent tingles down Dan’s spine. He was already excited for the day despite not being sure what exactly was in store for him.

“Good morning, Sir,” he responded quietly from where he was sat.

Dan didn’t know what he should do after he stripped when he entered earlier, so he decided to just wait in the same spot he sat on the previous day. He kind of wished there were steps to follow, like how was he supposed to act when his boss enters? He didn’t think even this could be hard. Perhaps he was overthinking, because it didn’t seem as if his boss was unhappy with him just sitting there. In fact, Phil’s face seemed to have softened when he laid eyes on him. Or maybe Dan was overthinking that too. He chewed on his bottom lip and twiddled his thumbs as he waited for some, any instructions.

Phil wanted to train Dan to be able to take all of him, and judging from the previous day, Dan was equally eager to be able to do a proper job. He would still go slow on his boy, based on how nervous he seemed. Even though Phil wanted nothing more than to shove himself down the boy’s warm throat. He just kept telling himself that he’d have lots of time for that once Dan was trained proper, he didn’t have to worry. Despite how nervous and awkward Dan looks, Phil felt sure that Dan wouldn’t be quitting any time soon.

“Could you be a darling and make me a cup of coffee please?” Phil requested as he settled down at his desk.

Dan nodded and hurriedly stood up, rushing to the mini pantry. Phil looked on at his beautiful view of his assistant’s perky butt. He couldn’t wait to fuck that ass raw, but he had to be patient.

Meanwhile, Dan was having a near meltdown trying to make his boss’s coffee. He was just too damn shy to ask how Phil would like it. After staring at the sugar and creamer waiting for some sort of direction from Phil that didn’t come, he decided to just leave it black and bring the sugar along.

He knows that his boss was really nice, but he still couldn’t shake the nervous energy off. Perhaps it was due to the vulnerability of being stark naked in front of such an important man, or how he really did not want to screw up and risk losing this weird as hell job.

“I uh,” Dan awkwardly gestured at the sugar packets after setting the cup down.

“Two next time, thank you,” Phil smiled up at him.

Dan nodded, making a mental note.

“C’mere,” Phil beckoned, and Dan timidly knelt before him.

“I’m gonna train you to take all of me, alright?” Phil asked, brushing back the curls on his boy’s head.

Dan nodded, keen on showing his boss that he can definitely do better than the previous day.

“Whoa not yet,” Phil chuckled when Dan moved to unzip his pants.

Dan quickly retracted his hand. Damn it he should’ve known to wait for permission.

“Get under the table. And get comfy, you’re gonna be there a while.”

Phil left as Dan crawled under the desk. The desk was so huge that there was enough space for him to sit up on his heels under it. Before Dan could start wondering where his boss went, Phil returned with one of the cushions from the couches.

Phil placed the cushion on the floor and Dan gratefully kneeled on it. As Phil sat down and bracketed him, Dan realised he had a view of only his boss’s crotch. He was effectively in between Phil’s legs, and he could barely see anything else. He peeked up and saw Phil staring back down at him.

“You’re going to be my lil cockwarmer today, yeah? No sucking. No blowjobs, just keep as much of me in that pretty mouth for as long as you can.”

Dan swallowed, already getting turned on by the idea. He slowly unzipped Phil’s pants when finally given permission, and tucked Phil out of his underwear.

“Stay still. Only move off when you really need to, understand?”

"Yes, Sir,” Dan spoke quietly before moving to wrap his lips around Phil’s head.

“Remember the safe gesture?”

They’d come to an agreement on their safewords and safe gestures in the contract. Dan snapped his fingers twice, and Phil nodded, looking pleased.

Phil was only half hard, so Dan easily got all of him in his mouth. He pressed his nose against Phil’s crotch, tickled by pubes. But he was determined to show his boss that he could do better, so he relaxed his jaw and stayed still.

As time ticked by, Dan found that it was getting harder to keep still. Phil was steadily growing in his mouth and he could feel his lips being stretched around the base of Phil’s cock. Dan breathed heavily through his nose and tried his best not to give him any stimulation, just letting his cock rest heavily on his tongue.

When Phil finally got fully hard, Dan felt his tip hit the back of his throat and had to move back a little. He could feel his gag reflex acting up and did not want to gag on his boss on only his second day of work.

Phil didn’t pay attention to him one bit. At one point, Dan even heard him make a phone call. Dan wondered how Phil was able to concentrate on his work when he’s hard and throbbing in Dan’s mouth.

Dan had given a fair share of blowjobs in his life, but he’d never been a literal cocksleeve before. He shifted his weight on the cushion uncomfortably, wondering how much time had passed, how much more time will pass before he’d be let off.

He tried to slowly move back down until his nose pressed against Phil’s crotch again, but couldn’t reach there just yet. He swallowed, and that was the first time Phil looked down at him since the start of the scene.

“When I told you to stay still I mean it. No stimulation at all, got it?”

Dan’s eyes widened and he tried his best to nod. A little saliva dribbled out the corner of his mouth just then, and Phil gave the smallest fond smile before returning his attention to his work.

Soon, Dan’s jaw began to ache. Without being able to swallow, he was drooling uncontrollably down his neck. He still tried his best to reach the base of his boss’s cock, but he couldn’t last longer than a few seconds before having to shift back a bit. This was the only movement that Phil seemed to be okay with, and he supposed that this was the purpose of the task after all. He hoped that he’d soon be able to take all of Phil in without having a gag reflex.

Dan was very hard as well. He hadn’t known that being used like this turned him on this much, plus the lack of attention from his boss made it even hotter.

His toes felt numb, and his knees and jaw were aching. He so badly wanted to touch himself, or to shift his position just a bit. But above all that, he wanted to be good for his boss. So he remained still and dug his nails into his thighs so as not to touch himself. He hoped that he’d be worthy of an orgasm later.

Dan ignored his aches as best as he could, focusing instead on the weight resting on his tongue, on breathing steadily through his nose, on his boss’s musky scent. He ignored the scratchy feeling forming at the back of his throat and instead focused on relaxing his throat further to keep trying to take all of his boss in his mouth. Dan closed his eyes as he fell into a rhythm of taking all of Phil in his mouth until Phil’s tip grazed the back of his throat, until his nose pressed against Phil’s crotch for a few seconds before moving back a bit. He tried to stay longer every time he moved back down.

As Dan moved back down, feeling Phil’s tip hit the back of his throat again, precum unexpectedly leaked. Dan sputtered and coughed, moving off of Phil entirely as his gag reflex kicked in. Phil looked down at him, looking a little concerned.

“Woops, sorry about that. Do you need to stop?” Phil asked, moving back a bit to give Dan some room.

Dan didn’t want to stop, though. He didn’t want to until he perfected being able to deepthroat his boss. It’s almost become a pride thing; he didn’t want to give up and be only average at what he’s supposedly best at.

“No no I’m sorry,” Dan spoke, voice rough and scratchy, as he quickly sat back up to get Phil’s cock back in his mouth.

Phil threaded his hand through Dan’s hair as Dan settled down again. Dan enjoyed how Phil rested his hand gently on his head for a while. In that moment, he realised that he had never wanted to seek approval from someone as much as he did from his boss. He wanted to do his best, as he felt that his boss only deserved the best. And right now he felt that his current best was not enough.

So Dan ended up staying still for almost another half hour. He was honestly impressed that Phil could stay hard in his mouth for that long. Right after another phone call, Phil brought his attention to the boy between his legs again.

Dan blinked up at his boss, eyes teary. He was sure that he looked a mess; he felt flushed and had saliva and sweat running down his chest and pooling on his crotch mixed with his own precum.

“You look so pretty like this, your lips so nicely stretched around me,” Phil commented softly, tracing a finger on Dan’s obscenely stretched red lips.

Dan whined low, Phil’s voice and praise turning him on immensely. He loved how even though he was technically just being used, his boss didn’t make it feel that way. 

“Guess I’ve teased you long enough, huh?”

Dan nodded and continued whining. His boss’s musky scent was intoxicating and it was driving him crazy how he couldn’t just swirl his tongue around the throbbing weight in his mouth, how he couldn’t suck and swallow around it.

But apparently his boss wasn’t going to give him what he wanted, as he moved back and off of Dan completely. Dan moved forward to chase after his cock almost instinctively, but Phil gripped his hair loosely and held him in place.

Dan licked his lips, looking desperately at the cock slick with his saliva in front of him.

“I wanna see if you’re as good with your hands as you are with your mouth,” Phil explained, pulling on Dan’s hair a little to tilt his head up to look at him.

“Yes, Sir,” he replied, his throat feeling a little sore as he spoke.

He knelt up, wrapping one hand on the base of Phil’s cock. He began to stroke Phil’s cock, twisting his wrist on the upstrokes and thumbing on the tip. His other hand wrapped around Phil’s full balls, cradling it. He gradually quickened his strokes, noting the way Phil’s breathing got heavier.

“Feels so good, boy,” Phil encouraged, resisting the urge to buck his hips into Dan’s hand.

Phil couldn’t possibly last much longer, especially after spending about an hour in Dan’s mouth. He warned his boy that he was close, which only made Dan speed up his movements even more.

Dan squeezed the base of Phil’s cock, giving the right amount of pressure and friction that he knew would drive anyone crazy. And just as he predicted, Phil came all over his hands. He looked up as he continued stroking his boss through his orgasm, hands now slick with cum. He observed how Phil’s eyes shut and mouth dropped in pleasure, how he groaned low in his throat and how his chest rose and fell rapidly.

Phil looked down at his boy through half lidded eyes as he came down from his high. Dan suddenly felt bold as the striking blue eyes landed on him again, and he let go of Phil’s softening cock to bring his hand up to his mouth. He stared up at his boss with wide innocent eyes and began to lick his hand clean, lapping up his boss’s cum.

Phil felt as if his breath was knocked out of his chest when he saw what Dan was doing. The sight was so hot that he felt as if he could come again.

“You like that, boy? Tasting my cum on your hands,” Phil asked, voice slurred.

“Uh-huh,” Dan whimpered and nodded, making a show of sucking each of his fingers clean.

“God, you’re so hot,” Phil uttered under his breath, but Dan heard it loud and clear and hid his smile behind his hand.

“Well done boy, that was so good. You did so good I’m proud of you,” Phil praised, stroking Dan’s sweaty curls.

“Thank you, Sir,” Dan almost purred, leaning up into Phil’s hand in his hair.

“Go clean up,” Phil said as he noticed how Dan’s chest was glistening with his drool and drying precum.

He helped Dan steady himself as he stood on shaky legs. He deliberately ignored Dan’s hard on, amused by Dan’s slightly disappointed expression when he realised he wasn’t getting rewarded immediately.

But Dan obeyed his boss’s instructions and cleaned up in the toilet, trying his best not to just jerk off in there. When he went back out, Phil was already focused on his computer, so he decided to read the newspaper laid out on the coffee table to distract himself from his hard on.

By lunchtime, he’d gone completely soft so Phil didn’t bother helping him out like he did the day before. Dan would ask for it but he knew his place, and strangely he found that helping his boss orgasm was somehow satisfying enough even if he won’t get the same pleasure in return.

Phil asked Dan to come along with him for lunch but Dan was certain that no one outside the room was aware of his presence, so it’d be weird if he were to suddenly emerge from the room and he wasn’t ready to face that situation yet. So Dan opt to stay in Phil’s room and Phil brought back lunch for him. Phil apparently did not care if people knew about him or not, which made Dan wonder if he  _did_  have personal assistants before. He’d have to ask about it when he found the right time.

* * *

Dan realised he got bored real easy. Phil mostly used him in the mornings, and he always had nothing to do after lunch. Of course he couldn’t expect Phil to be playing with him throughout the entire day - he had an actual job to do. But Dan didn’t complain, couldn’t complain. Not when he was being paid so much to have sex and then just sit around and look pretty. He couldn’t help but wish that Phil wasn’t taking things this slow, though. Based on his contract, he knew that Phil wasn’t even making him do 10% of what was required of him. Not yet, anyway. He couldn’t wait to move on to all the kinks listed on it.

But Phil seemed determined to train his mouth before going any further. The next day, Dan spent his morning on his knees being a cockwarmer again. This time, Phil fastened a spider gag on him, opening his mouth wider and leaving him no choice but to lock his jaw in place. Dan didn’t like how he couldn’t wrap his lips around Phil’s cock, but he did feel his gag reflex slowly going away.

He did enjoy how Phil was slowly starting to go a bit rough on him. He was still very gentle; hand lingering on his hair and soft strokes on his cheek. But he also tugged on his hair a little more, even pushing his head down to the base of his cock and keeping him still there for a while. Dan moaned throughout, loving the new treatment and hoping his response would encourage Phil to go rough on him more often. He did love Phil’s soft touches, but deep down he was simply a masochist who craved for someone like Phil to dom him completely.

Phil had ordered him to jerk himself off in front of him afterwards. Dan was painfully shy at first, but then he tried to ignore the fact that Phil was his fucking  _boss_ , and instead pretended that he was just another hot hook up. Phil had certainly enjoyed the show Dan put on for him, full of desperate whining as he stroked himself on the rug until he came all over his stomach.

The rest of the week went pretty much the same. Dan found it easy to fall into routine. Enter the office, strip, sit on the floor. Greet his boss when he arrives, make him coffee, slip under his desk. Train his gag reflex away to take all of his boss in his mouth. Spend the rest of the day just chilling and drinking hot tea to soothe his throat. Occasionally help fetch items from the other end of the room when his boss asks him to. Leave only when the coast is clear at the end of the day.

* * *

Before Dan knew it, two weeks flew by and he was successfully able to deepthroat his boss without his gag reflex anymore. Dan was a little surprised that he made it this far without screwing anything up. His boss seemed happy with him, and he was also warming up to the man real quick. He was glad that all the nervous energy surrounding him at the beginning was wearing off as he got used to his out of the ordinary job.

On days when Phil didn’t grant him any relief at work, he’d spend his night jerking off to the memories of Phil using him earlier in the day and the image of how he wishes Phil would use him. And if he allowed his mind to entertain forbidden thoughts long enough, he’d admit into the darkness of his room that maybe,  _maybe_  he’s starting to fall for his boss.

**Notes for the Chapter:**

> Thank you for all the love on the first chapter and I hope you enjoyed this one too :)


	3. Chapter 3

Dan cursed himself as he ran towards the office. His head was still pounding from his hangover, but it was the least of his worries at the moment. He knew he shouldn’t have gone to the club the night before, he knew it was a bad idea. And yet there he went, back on his bullshit again. He’d been doing so well on his job the past weeks as well. The last thing he wanted was to disappoint Mr Lester.

He rushed into the office, stopping in his tracks when he realised that there were already people in. He was so used to being the first in. He avoided eye contact with everyone, keeping his head down as he walked hurriedly to the big door at the end of the office. He felt curious eyes on him and wondered if anyone already guessed right who he was, his place in this office.

He put his key into the lock of the door to his boss’s office only to find it already unlocked. Dan gulped, slowly turning the doorknob. He had no idea how his boss would react to him being an hour late. He really should’ve just stayed home and called in sick. Why didn’t he think of that earlier? Damn it.

Dan quietly stepped inside, and saw Phil already sitting at his desk. Phil didn’t bother to even look at him. Dan bit his lip anxiously, somehow feeling even more disappointed in himself when he noticed that Phil already made his coffee himself. He stood quietly, waiting for Phil to say something. But Phil continued ignoring him so he had no choice but to speak up first.

“G-good morning,” Dan’s voice was barely above a whisper.

“Care to explain?” Phil answered, still not looking at him.

“I’m s-sorry Sir I.. Overslept,” Dan stuttered, still standing by the door.

Phil finally turned towards him, but his nonchalant look made Dan even more nervous.

“You remember what’s stated in the contract for not following my rules?”

“Y-yeah uh, a punishment you deem fit,” Dan answered, his heart beating fast as he wondered what sort of punishments Phil would mean.

“Strip and bend over my desk,” Phil sighed and got up, sounding almost annoyed.

Dan gulped as he quickly got rid of all his clothes, then he placed his palms flat on his boss’s desk and bent a little, his ass feeling exposed.

Phil had gone to take something out of a drawer at the side of the room. As he slowly walked back to his boy, he could see just how nervous he was. He stood behind Dan, so close that his shirt almost brushed against Dan’s skin. He noticed how Dan was trembling slightly. Without warning, he grabbed onto Dan’s hair and pushed him down, until Dan’s cheek was pressed against the cool surface of the table and he was properly bent at the hips. 

“This is what I mean by bend over.”

Dan winced a little when Phil grabbed his hair, not expecting to be pushed down. Phil’s voice was so authoritative and Dan knew he was getting punished so was it weird that he was getting turned on by this?

“Yes, Sir,” he whispered belatedly.

Phil stood by the side Dan was facing away from. He twisted the paddle in his hands, studying the pretty freckles dotted around his boy’s back. He softly rested the paddle against his boy’s bum, just to let him guess what he was going to be punished with. He heard a gasp so soft it was almost inaudible, but it only got him more excited.

So perhaps Phil was a sadist who had been waiting for his boy to slip up somehow just to have a reason to spank him. But Dan had been a near perfect sub since day one, and although he was disappointed when he opened his door to an empty office earlier, it quickly turned into anticipation to finally be able to punish his sub. He loved how obedient Dan was, but he also loved having to deal with occasional moments of rule breaking too.

He rubbed the paddle across Dan’s ass for a bit, tapping it lightly to build up the anticipation. His soft taps gradually grew into the first actual hit, the sound of the smack resonating around the room.

Dan bit his lip at the first spank, biting back a whimper. He’d been spanked before, but never as a punishment. In fact, he’d never been punished before; he’d never had a relationship with a Dom. Playful spankings with random hookups couldn’t compare to the emotions that tie in with the spanking he’s facing now. He felt his cheeks heat up, and he couldn’t decide if this was all more enjoyable or humiliating.

“Count.”

At that command, Dan decided that it was both equally humiliating  _and_  enjoyable, and he didn’t even know it was possible.

“One,” his voice was unintentionally shaky.

Almost immediately, the paddle landed on his ass again. Dan gasped and jerked forward into the desk a little at the unexpected hit.

“Louder.”

Phil’s assertive voice caused the hair on the back of Dan’s neck to stand. He cleared his throat and made sure to be louder as he said  _Two_.

Dan grit his teeth throughout the spanking. He so badly wanted to rub his sore ass or touch his hard dick, but he clenched his fists on the desk instead. He couldn’t quite believe how incredibly turned on he was. Were punishments meant to be enjoyed?

Phil didn’t hold back on his swing. He loved the way his boy’s ass bloomed pink. He loved the little gasps and muted moans, the way his boy jerked forward a little at each hit. He especially loved how his boy was so hard and leaking, clearly enjoying his punishment.

Halfway through the spanking, Dan found himself tearing up. From the pain or humiliation or the guilt of disappointing his boss, he wasn’t sure. He’d never experienced such an emotional spanking before, and the newness of it all was overwhelming. He sniffled a little before gasping out a  _Ten_.

Phil was impressed with how well his boy was taking the punishment. He was accepting it quietly instead of giving any protests that Phil was expecting. Dan didn’t even try to block the spanking with his hand or rub at his sore ass, which Phil had experienced with his old subs before. In fact, Dan even stuck his ass out a little more whether he realised it or not, definitely eager to receive the next hit. Phil was in awe with his obedience, and he knew that Dan definitely was not late on purpose.

He alternated the spanks between each cheek, watching Dan’s plump ass bounce from the impact. Phil could hear little sniffles, and was happy that the point of the punishment was coming across.

“Twenty,” Dan moaned out, the stinging pain on his ass ironically shooting pleasure up his spine and straight to his cock.

Dan felt the paddle being placed on his back. He sighed when his boss’s hand started rubbing on the sore skin, soft and soothing touches that calmed him down. His hand felt cold against his warm and red skin.

“Next time I should give you one for each minute you’re late,” Phil’s voice was still harsh unlike his gentle touches.

“I’m really sorry Sir, I didn’t mean to be late,” Dan whined pathetically.

Phil removed the paddle from Dan’s back and placed it on the desk. He held onto Dan’s shoulder and pulled him to stand straight and face him. 

Phil’s heart leapt at the sight of his boy. They were the same height but somehow Dan seemed smaller, especially with the way he hunched in on himself. Dan looked up at Phil guiltily through red rimmed eyes. His bottom lip was a matching red from being bitten so hard during his punishment. His dick was throbbing but still he was being a good boy keeping his hands by his sides, not even moving back to rub his sore ass. Phil loved the sight of his poor boy in front of him.  _Fuck, I really am a sadist_ , he thought.

Phil opened his arms welcomingly and brought his boy into a hug. He rubbed his back softly and threaded his other hand through his boy’s curls, gently pushing his head down to rest on his shoulder.

Dan stood pliant for a moment, but as he adjusted to the stark contrast of these soft touches compared to the harsh spanking mere moments before, he slowly brought his hands up and meekly wrapped them around his boss’s waist. He sniffled into Phil’s shoulder, breathing in the cologne he’d become so familiar with.

“You did really well for your first punishment,” Phil praised softly into his ear as he rubbed circles into his boy’s back.

“Thank you,” Dan whispered, “I promise I won’t be late again, Sir.”

“I trust that you won’t,” Phil replied as he let go of Dan.

Dan stared up into the icy blue eyes. But he could see warmth in them, maybe fondness and if he dared himself to think about it, even love. He subconsciously moved closer, their faces so close that he could feel Phil’s breath on his nose.

But as Phil stepped back, he realised that of course Phil wasn’t going to kiss him. He wiped his cheeks, mentally scolding himself for even thinking about a kiss. Why would Phil kiss him when he’s technically just an  _employee_.

“I’ll let you rest now, yeah?” Phil said, already sitting back down at his desk.

Dan nodded, mumbling a thanks. He went to sit at the couch by the coffee table, but realised quickly that the scratchy material against his tender ass wasn’t a good idea. So, he awkwardly moved to lie on his stomach on the rug.

But that was a bad idea too. The friction of the rug against his dick was so sweet, and he instinctively started to grind down onto the rug. He kept his movements small so as not to alert his boss even though it was barely enough.

Phil ignored Dan for a while, letting his boy think that he wasn’t aware of what he’s doing. No matter how small his hip movements are, Phil could clearly see and hear what Dan was doing. He always left Dan alone but he did keep an eye on him, and Dan was oblivious most of the time to his hyper awareness of what his boy was up to.

After a few minutes of Dan struggling to get off on the rug, Phil finally decided to pipe up.

“Was the punishment not enough? Do you need a reminder of another rule?”

Dan gasped and scrambled to sit up. His sore ass grazed the rough material of the rug but he could barely feel it when he was now in shock that he’d been caught. But honestly he should’ve known how unsubtle he was being. Phil’s gaze was still focused on his computer.

“N-no Sir,” Dan answered softly, “I’m sorry.”

His dick twitched at the sudden lack of stimulation. He clenched his fists at his sides to keep from touching himself.

“I’ll let it slide,” Phil side-eyed him, “for today.”

Dan blinked, feeling his eyes water. He really did not mean to be naughty. He’d been on his best behaviour since the first day, and he was disappointed in himself for suddenly breaking rules today. He really shouldn’t have gone drinking yesterday, damn it.

He sat in silence, not caring that his ass still felt tingles of pain against the rug. He used to go to bars or clubs every weekend, getting random hookups for the hell of it, mainly to cover up his loneliness for the night. But no matter how much he’s sticking to that reason for going back last night, he damn well knew that it wasn’t the case anymore.

He’d gone there to take his mind off of Phil. His fucking boss. Who he absolutely cannot fall for. But it just got worse when he started comparing the men there to Phil, and thinking how they’re all no match to Phil. He realised that all he wanted was Phil. And for some reason he felt like if he were to carry on with a one night stand, it’d be as if he’d be cheating on Phil. Which he knew is silly, because for all he knew, Phil could be having random hook ups on the weekends too. But he still felt wrong. So he opt for the next best option: to drink his thoughts away.

Now his hangover was slowly disappearing, but all he’s left with is a strange feeling for his boss that he couldn’t quite describe. He barely knew his boss still. He knew him pretty well in terms of his turn ons, his sensitive spots, the way his breathing goes ragged when he’s about to come. But he didn’t know a single thing about this man’s life outside the office. How the hell could he be falling for someone who was technically a stranger?

And Dan was sure that his feelings weren’t mutual anyway. If anything, the little rejection of his kiss earlier confirmed it. So he had to be professional and just suck it up and do his job. The less he dwelled on it, the better. So he busied himself with scrolling through social media on the rug to let the time pass.

* * *

Phil always invited Dan out to lunch, but Dan always refused. He still didn’t want to go out and face the other people in the office, especially now that some already saw him this morning. So Phil would always bring back lunch for him, sometimes even just ordering in and spending his whole lunchtime with him.

Today, Phil ordered in again and they were sat around the coffee table eating their pasta.

“Why do you always spend your lunch with me when you could be out with your other colleagues?” Dan asked quietly, not sure where the thought came from but needing to know the answer.

“If you wanna be alone I can leave for lunch next time,” Phil said, and Dan couldn’t tell if he heard a hint of hurt in Phil’s voice or if he imagined it.

“No I mean… I don’t know, isn’t it boring to stay in here all day? I’m not exactly much fun company anyway,” Dan said, twisting his fork into his pasta.

“I like your company, Dan. Even when it’s quiet. I like how we don’t have to fill the silence with small talk all the time, like what I’d have to face with the people out there,” Phil made a face of disgust, “Anyway I’m their boss. They’d hate for their boss to join in their free time.”

“True,” Dan nodded, recalling awkward lunches with old bosses.

“It’s the same for you, isn’t it? I should’ve taken the hint,” Phil sighed.

“No no that’s not what I meant at all! I just asked because I didn’t want you to feel obliged to keep me company,” Dan quickly explained. He’d much rather have his boss’s company than be alone during lunch, but he just didn’t want to feel like a burden.

Phil nodded and smiled a little, and the conversation ended there. What used to be comfortable silence between them now felt awkward, and Dan regretted even opening his mouth in the first place.

Dan felt too awkward to not try to ease the tension in the air, so he decided to start another conversation.

“So..I realised we kinda don’t even know each other much,” Dan slowly started.

“That’s true,” Phil chuckled, “Well whadaya wanna know? I’m pretty boring to be honest, but I’ll answer anything you got on your mind,” Phil was seemingly eager to ease the tension as well.

Dan wanted to start the conversation slow and simple but he was too damn curious not to start with the question bugging him since day one.

“Is this like…a normal thing in your office?” Dan slowly asked, gesturing his naked form.

He wasn’t even shy about being naked all the time in the office anymore. He got used to it pretty quickly, and perhaps he even enjoys catching Phil checking him out throughout the day.

“I’ve had one before you, yeah,” Phil responded, not giving much else information.

Phil’s answer just piqued Dan’s curiosity even more, but he didn’t know if he should continue prodding since Phil didn’t seem willing to elaborate for some reason. So he changed the topic, instead asking Phil about his hobbies outside of work.

Dan was surprised to learn that unlike the perpetual Dom he imagined Phil to be, Phil was instead just a normal accountant by day, but an absolute nerd by night. Phil loved all the video games he loved, they shared similar music tastes, and Phil even watched some shows that Dan liked as well. They had way more in common than Dan expected, and he ignored the strange feeling of butterflies in his stomach as he excitedly discussed their favourite band.

“You’re not boring at all,” Dan said as they ended lunch.

“Glad to hear that,” Phil smiled, helping Dan clear their dishes.

Before Phil returned to his work, Dan suddenly remembered the question he had in mind earlier before sidetracking.

“Wait, so what happened to the… the one before me?”

“He uh, just lost interest and found another job,” Phil shrugged, sitting at his desk and quickly ending the conversation.

Dan wondered why Phil was so tight-lipped about his previous personal assistant. But even more, he wondered how the previous guy could leave this job. How was the money not good enough for him to stay? Or maybe the guy had more dignity than himself, Dan thought.

Dan went to lay back on his rug and spent the rest of the day wondering if it was even possible to ever lose interest in the wonder that is Phil.

**Notes for the Chapter:**

> thank you for your comments and kudos <3


	4. Chapter 4

**Notes for the Chapter:**

> yes I know I accidentally went on another hiatus yet again, but at least I'm back before dan in 2k19 I guess that's an achievement? lol

Phil was pleased to enter his office and see that his assistant was punctual the next day. He smiled as the boy sitting on the rug greeted him softly, still ever so shy. The smell of the coffee already made for him was so inviting.

“Why don’t you make yourself a drink too?” Phil asked as he sat on his desk.

“I may have had a coffee before you entered,” Dan admitted quietly.

Phil smiled, glad that the boy was getting comfortable enough to do his own things while alone in the office. He settled down with his coffee and spent a while reading his emails.

Dan realised that he still couldn’t quite predict how his days in the office would go. Even when Phil was training his deepthroating, he’d change it up a bit each time. He had no option but to sit and wait to see what he’d be spending his day doing.

After Phil finished his coffee, he finally addressed Dan again.

“From your video I assume your ass won’t need training like your throat, right?” Phil chuckled a little.

Dan was confused for a moment before he remembered what video Phil was talking about. He tried so hard not to cringe as his mind replayed the first day he met Phil. How Phil boldly watched the video of him taking two dicks up his ass right in front of him. How that was the first time a stranger watched a sex tape of his. And how strange it is that the stranger is now his boss.

Phil almost cooed aloud looking at how cute Dan was, his cheeks turning pink in embarrassment at the mention of his video.

“I’d still like you to be ready for me, though,” Phil said, standing up and gesturing over his desk, “C’mere.”

Dan quickly stood up and bent over the desk - properly this time. He gasped lightly when he felt cold but gentle fingertips rest on his ass. Phil’s fingers slowly traced the curve of his ass, tickling his skin. Dan wondered if he was finally going to be fucked by his boss. He couldn’t wait and he’d be lying if he said it wasn’t on his mind most days.

The light touches stopped as Phil went to the drawer that Dan has learnt stored all his play things. Dan stayed still despite growing curious as to what Phil was retrieving.

When Phil came back, he took his time exploring more of Dan’s skin. Dan shuddered slightly as Phil stroked his back, from his shoulder blades to the dimples above his ass.

Phil felt goosebumps rising on his boy’s skin everywhere he touched. Slowly, he moved lower to Dan’s ass crack. Dan eagerly stuck his ass out, making Phil smile. Phil continued lower, his fingers sliding between Dan’s cheeks until he felt his hole.

Dan gasped as he felt Phil press against his hole. Slowly, the fingers began to pry his cheeks apart. Strong warm hands holding his ass as one finger explores his hole. Dan tried his best to relax and let Phil’s finger in.

He cleaned himself every morning before going to work as per Phil’s orders. He was proud of himself for improving his shaving skills down there too, spending less time in the bathroom every week. But somehow he still felt nervous as his boss inspected him, feeling as if he might not have done a good enough job. But his boss didn’t say anything as he let go, so Dan sighed quietly in relief.

Dan couldn’t help but jerk a little in surprise when the fingers returned, cold and wet this time. Phil placed a soothing hand on his back and slowly pushed his lubed finger into Dan.

“So tight, hard to imagine that your little hole took two big cocks,” Phil chuckled as he pumped his finger in and out.

“I’m just really good at taking cock,” Dan was really good, and in that moment of boldness he wanted Phil to know what a shame it was that Phil had been denying himself of Dan’s ass this long.

“Oh really?” Phil chuckled, loving his timid boy’s sudden feisty spirit. He took the opportunity to insert two more fingers alongside his index.

Dan wanted to respond with something witty again but ended up biting his lip to stifle the unexpected moan that escaped. Phil was going slower than Dan was used to, and it felt foreign. Dan was used to quick, desperate fucks. He never had someone pay so much attention to detail; pay attention to him this way. His own cock was growing impatient, but he realised that he quite enjoyed this slow pace.

When Phil brushed against his prostate, he didn’t bother trying to keep himself quiet. Phil smirked as Dan moaned loud. He noticed just how hard his boy was, how his breathing had gotten heavier. His boy thinks he’s really good at sex? Well he’s not ready for what Phil could do to him. Phil pressed against his prostate again just to get him more worked up.

Phil took his fingers out and Dan was more than ready for Phil to get in him. He needed it more than he needed air at the moment. He felt himself leak precome. He almost left his bent position to look behind him and beg for Phil to hurry on with it. But although he had no doubt that Phil would love to see him be desperate, he thought that Phil would appreciate it more if he was obedient and stayed still. So he pressed his cheek harder against the desk and waited with bated breath.

He was so certain that Phil was going to fuck him that he was surprised to feel something cool against his stretched hole instead. He felt a buttplug push into him, much shorter than Phil but almost as thick. Phil patted the end of the plug once it was fully inside Dan.

“There we go, now you’ll be ready for whenever I want to take you,” Phil said, satisfied. He then lightly smacked Dan’s ass, indicating for Dan to stand.

Dan slowly stood up, trying to hide the disappointment from his face. He wanted to tell Phil that he was more than ready to be taken, had been ready since the start of this weird job. But of course he had to just be patient and go with Phil’s pace.

And just as he suspected, Phil completely ignored his hard and aching cock. And he was left with his ass plugged the whole day and no more attention received until Phil took it out before leaving at the end of the day.

* * *

 

That became their morning routine over the week. But Dan still couldn’t really predict what would happen, because Phil used a different toy every day. He wondered just how many dildos and buttplugs Phil could possibly own. He had such a variety up his ass over the week; short and wide, long and thin, grooved, you name it, Phil probably has it.

His least favourite was the long and wide one. He did love how it filled him up at first, but it was rather uncomfortable by the end of the day. Other than that, he did love being plugged everyday. The only thing that would be better was if he was being filled by Phil himself, or if Phil paid him any attention at all the rest of the day after plugging him up.

Phil always slowly got Dan worked up by his light touches all over his body and his slow fingering before pressing the plug right up against his prostate. Phil never gave him permission to come, but Dan didn’t complain. He’d just subtly shift himself so it wouldn’t press against his prostate all day. Though he always had to rush home to get himself off.

On Friday, it seemed like just another day of their new routine. The buttplug seemed like a fairly okay one, nothing Dan couldn’t handle. It wasn’t that long and it was the perfect girth to be enjoyable for Dan.

He was laying on his side on the rug when all of a sudden, a jolt of pleasure shot up his spine. Dan yelped in surprise, realising that today’s plug was also a vibrator. He looked at his boss with wide eyes, but Phil paid him no attention as usual. In fact, he looked too busy to even play and Dan started to wonder if he had imagined the one second of vibrations.

But before Dan could second guess himself, the vibrations came again. He bit his lip as the vibrations sent pleasure straight to his already hard dick. He shifted a little on the rug, whimpering when the vibrator brushed against his prostate. The vibrations didn’t stop this time, instead a steady buzz continued in his ass.

Dan dug his nails into the rug to stop from touching himself. After a few minutes and just as he got used to it, the vibrations started going off at a random pace. He couldn’t help the little whimpers that escaped his parted lips as the vibrator pulsed in his ass, sending pleasure in waves.

“What is it?” Phil finally acknowledged him after Dan let out a particularly loud whine.

Phil sounded so genuinely clueless that Dan thought that Phil could try an acting career if he was tired of his current job.

“Sir, the vibe...” Dan whined, unable to continue his sentence as he focused on not touching himself.

“I knew you’d like it,” Phil smiled, then promptly returned his attention to the computer.

Dan had expected Phil to continue ignoring him, so he just clenched his teeth and shifted on the rug more. Just as he thought Phil couldn’t get any cheekier, the vibrations became more intense.

“Sir pleaseee...” Dan panted.

“What do you want?” Phil asked, barely able to keep a straight face this time.

“Please touch me,” Dan asked desperately, almost thrusting his hips into the air.

“I’m busy, boy,” Phil said, sounding fake apologetic.

Dan almost glared at him, but he knew better. Just as he was about to beg again, there was a knock on the door.

Dan looked at Phil in shock. Phil stared back at him, waiting for Dan to decide if he wanted to stay. But he knew that Dan wouldn’t want to, he had always hid in the bathroom when people entered his office even though Phil told him he didn’t have to. Phil knew that Dan wouldn’t want to stay especially in his current state; so hard and desperate and vulnerable.

Dan got up on shaky legs and ran for the bathroom. Just as he closed the door, he heard Phil calling for the person to come in. He could feel the vibrations get slower, probably to the lowest setting. He was grateful that Phil at least wasn’t going to leave him be a desperate mess on the edge of coming in the bathroom.

“What are you doing, Phil?”

Dan could hear the voice of a man. He didn’t mean to eavesdrop, but it wasn’t like he was consciously putting an effort to when the man was so loud.

“I don’t mean that! Don’t act stupid.”

While the man was loud, Phil was so soft that Dan couldn’t hear him at all, so he couldn’t exactly understand the one-sided conversation.

“We all saw him on Monday.”

Dan held his breath. Was the man talking about him? He felt like the entire office saw him entering the office late on Monday.

“Why are you doing this again-”

Dan couldn’t hear the rest of the conversation; it seemed as if Phil had asked the man to quieten down.

Dan gulped. He tried so hard to be invisible but because he was late once, everyone knows about him now. He guessed that he would be found out sooner or later anyway and there was probably no point hiding. It’s not like Phil actively tried to keep him away either. He’d been hiding because he was too shy to face anyone more than anything else. But why was this person so bothered about his presence in the office?

Dan wondered if it had anything to do with the previous personal assistant that Phil had. He waited in the bathroom for quite a while, his mind swimming with questions.

His thoughts were soon interrupted by the vibe in his ass increasing its vibrations again. His boner had died down a little when his mind went wandering, but now he remembered his original problem: his need to come.

He took the increasing vibrations as cue that the man had left the room, so he slowly opened the bathroom door and peeked out. He slowly walked over to Phil when he saw that the coast was clear.

Phil seemed unbothered by whatever exchange happened with his coworker, but Dan still felt the need to help his boss relax somehow. He wasn’t sure if Phil wanted to do anything though, so he just knelt by his chair.

Phil looked down at him and smiled, “Glad that you didn’t use that as an opportunity to get yourself off.”

“I would never break your rules like that,” Dan replied, almost offended that Phil thought he would disobey his rules.

Dan felt the vibrations in his ass stop entirely.

“Do you need anything, Sir?” he asked softly, looking up at his boss with doe eyes.

“Looks like you need something more than I do,” Phil answered, but he felt touched that his boy wanted to serve him.

He had hoped that Dan didn’t hear anything, but by the way the boy was looking at him like he felt responsible to help him somehow, he was afraid that Dan might have heard more than what he’d like.

Dan did feel like he needed to help Phil, but he wasn’t sure exactly what Phil needed help with. From the little exchange that he could hear, it sounded as if the man was agitated and he just wanted to help Phil relax after such a conversation.

He didn’t know how to answer his boss, he felt like his own erection was unimportant at the moment. But before he could say anything, Phil continued talking.

“Just a little while more til lunch,” Phil said before turning his attention back to the computer.

Dan felt the vibrator start pulsing again, and just resigned to feeling somewhat guilty for being late that one time and letting the office see him which caused the conversation that he couldn’t help Phil with.

By lunchtime, Dan was aching with the need to come again. Phil had continued playing with the different levels of vibrations as he was doing before his colleague had entered.

Phil honestly just wanted Dan to forget whatever happened, but he had a feeling that his boy wouldn’t let it go that easily, even in his current state.

He walked over to his boy who was sweating and trembling on the rug with the need to come.

“Get on the coffee table for me, would you?”

Dan struggled not to touch himself, even just to stave off his orgasm. He was so on edge, he didn’t know how much longer he could last. But he managed to lie on his back on the table, wondering if he was finally going to get another of his boss’s amazing handjobs again.

His boss spread his legs apart and pulled him to the edge of the table enough to let his legs be bent at the knees. He admired Dan’s hard on twitching, a small pool of precum smearing his stomach. The vibrations in his ass continued relentlessly, and Dan felt like he could come if Phil so much as lay a finger on his neglected dick.

Dan widened his eyes in shock when Phil knelt down between his legs. With a glint in his eye, Phil locked gazes with Dan mischievously before going down on him.

Dan groaned out loud. His boss’s mouth felt so good around him, so wet and warm. Phil swirled his tongue around his tip and sucked hard, sending Dan into a series of moans and whimpers.

With what little coherence he had left, Dan warned Phil about getting close. He craned his neck to look at Phil bobbing on his dick. Phil didn’t stop, however, instead sucking even harder and even playing with Dan’s balls.

Dan so badly wanted the blowjob of his lifetime to last, but he couldn’t hold it in any longer. Phil wasn’t going slow at all and with the vibrator now pressed right up his prostate, he lost control.

Dan could see stars as he came, shuddering as he felt Phil swallowing around him. He gripped the edge of the table hard and moaned loud as he came. By the end of his orgasm, he felt so spent but at the same time, he’d never felt better.

* * *

 

Dan woke up on the couch. He blinked his eyes open and slowly sat up, looking around him. His lunch was on the coffee table. He looked over to the desk where Phil was sat doing his work.

He looked at the clock to see that 2 hours had passed since lunchtime. His boss must’ve carried him to the couch. He realised that his ass wasn’t plugged anymore either.

His heart ached a little. He had felt the need to take care of Phil after the conversation he had with his coworker and yet there he was, letting Phil take care of him instead.

“You’re finally up,” Phil said, chuckling a little.

“Thank you for letting me come today, Sir,” Dan answered shyly.

“Your lunch has probably gotten cold,” Phil said, ignoring what Dan had said and pretending as if nothing before Dan’s nap had actually happened.

Dan sort of wished he hadn’t fallen asleep after the orgasm, or he wished that Phil didn’t let him come at all, because he originally wanted to spend lunch asking Phil about what he had heard. Judging from how he hadn’t been allowed to come the entire week, he had a feeling that today was supposed to be no different until the colleague came and changed Phil’s plans. Maybe Phil thought to give him an orgasm so good it knocked him out so that Phil wouldn’t have to deal with any questions from him.

Dan sighed, they don’t even talk anytime outside of lunch so he’d just have to drop it and wait for the next opportunity to ask about it. Still, he couldn’t shake off the feeling of being bothered by what he’d heard even though he barely heard most of it. And he didn’t even understand why he was so bothered when Phil didn’t seem to care at all.

**Notes for the Chapter:**

> I'm rly so grateful for all of you who still stick around even when I take ten years to update, yall don't deserve having to wait so long but thank you for being so patient I appreciate it and I hope you enjoyed the update!!


	5. Chapter 5

**Notes for the Chapter:**

> STILL back before Dan :P

Dan felt so restless. He would’ve gone to the club again, but from the incident the past week and how it just reminded him more of Phil, it clearly wasn’t a good idea.

But the problem is that everything was reminding him of Phil now. He didn’t know how he’d let this happen to himself. He tried watching an anime but stopped when he ended up imagining how much better it would be to watch it while curled up against Phil instead. He tried making a cup of coffee but accidentally made it with two sugars even though he prefers his with only one. The worst part of all of this was that he couldn’t even get off anymore because it just doesn’t feel as good without having Phil’s permission first.

He couldn’t believe that he was actually looking forward to going to work. After giving up trying to watch some shows, Dan had spent the rest of his Saturday mulling over the conversation Phil had with his colleague. He wished he could meet Phil’s old assistant and ask him about his experience. Did the old assistant also accidentally form a weird obsession over Phil? Perhaps he had quit to regain the ability to go about his daily life without having Phil on his mind 24/7.

The next morning Dan decided to go out for a walk to clear his mind. He stopped by the bank and let his jaw drop for a bit when he saw the ten grand newly deposited into his account. It didn’t feel like a month had gone by already, and he still somehow hadn’t believed that Phil would really pay him that much for just sitting around most of the time.

He tucked his hands into his coat pockets as he walked through a park, letting the breeze mess his hair up a little. He hadn’t been to the park this early in the morning since, well, ever. He used to sleep well into the afternoon on weekends, but he can’t even do that anymore since he’s so used to his weekday schedule already.

Dan sat on an unoccupied bench and decided to people-watch to hopefully keep his mind off his fucking  _boss_. It was a nice day, the sun was out but the gentle breeze kept it cool. There were quite a few people in the park, many jogging and cycling, some just taking a stroll like him. Some people were laying on the grass having picnic brunches. He smiled as he watched some carefree kids running around playing tag.

Dan’s eyes laid upon a couple having a picnic. They were sat really close together, the girl almost on her partner’s lap. She was giggling as he tried feeding her a slice of cake. The guy looked absolutely smitten by her laugh. As she got the cake into her mouth, he managed to kiss her nose, causing her to laugh even more and swat his arm playfully before going for a proper kiss.

Usually Dan would look away in jealousy because he wished he could be happy and have cute dates with someone too. But as he turned away this time, he realised that he now had in mind who he wants that someone to be.

Dan groaned, startling an old lady walking by. He got up, deciding to leave the park, leave the happy kids and the happy people picnicking and the disgustingly cute couple on their stupid date that he wishes he could also have with Phil.

He walked past a coffee shop near the park. It always smelled so good, but it was a rather expensive little place. He always told himself that he’d try their coffee one day when he could finally afford it. He stopped in his tracks and decided that today would be that day.

The smell of coffee and cakes was even more enticing when he stepped in. The shop looked really cosy and there weren’t that many people inside, just a few enjoying a book with their coffee. Dan thought that this was actually a really nice way to spend a Sunday, rather than sleeping a hangover away after clubbing on a Saturday night. Perhaps his clubbing days should be replaced with coffee shop days. Especially since he could afford expensive coffee now.

He ordered his usual go-to drink to see if this place was really worth the price, or if it was just an expensive Starbucks. As he turned away from the counter and looked around to find a seat hidden in a corner where he could enjoy his drink without being seen by the world, his eyes landed on an all too familiar face.

Just as Dan thought,  _Am I really getting so bad that I’m hallucinating him right now?_ , Phil looked up from his laptop. His eyebrows shot up, mirroring the shock on Dan’s face.

But Phil’s shock was quickly replaced with a warm smile, and he beckoned Dan over to his table. Dan bit his lip, wondering if it was a good idea to sit with his boss, especially when he’s trying to  _not_  think about him. But Phil actually looked  _excited_  to see him, and he found his legs bringing him closer to Phil’s table before he could even think.

“H-hi Sir,” Dan said shyly.

“You’re not working right now, you don’t have to call me that!” Phil chuckled as he cleared his papers to let Dan place his coffee on the table.

Dan felt his cheeks heat up in embarrassment, but at the same time he somehow felt it wrong to call Phil anything other than that.

“Didn’t expect to see you here,” Phil said, smiling as Dan sat down. 

“Me neither, you come here often?” Dan answered.

“This is my favourite coffee place!” Phil nodded, adjusting his glasses that were slipping down his nose, “I love it here, and I usually spend my weekends here if I have work to do, it’s so conducive.”

“You gotta work on the weekends too?!” Dan asked incredulously.

“I lead a boring life, I know,” Phil said almost regrettably, “but I don’t hate my job, so I don’t mind. Do you come here often too?”

“It’s my first time here, actually,” Dan replied. He couldn’t believe the coffee shop he’d always wanted to try was Phil’s favourite shop.  _Of course_ it was.

“Oh! And you got the caramel macchiato? Good choice, that’s my usual drink,” Phil smiled as he looked at Dan’s drink.

It was then that Dan noticed that Phil also had a caramel macchiato. _Of course_ , Dan thought. Again.

“This is my go-to drink when I try new coffee shops,” Dan explained, “to see if it’s any better than Starbucks.”

“It’s definitely better than Starbucks are you kidding me,” Phil said indignantly, as if comparing this place with Starbucks was the worst insult he ever heard.

“I’ll be the judge of that,” Dan said before taking a sip.

Phil was eagerly looking at him, waiting for a reaction. The drink was really good, way better than a Starbucks. He could’ve maybe had a better first try of it if he didn’t have his boss staring at him with a “I told you so” look on his face.

“It is good,” Dan admitted, half wanting to smack the smug smile off Phil’s face and half wanting to just get up and leave before he fell further for that beautiful smile.

“Right?! I can’t go back to Starbucks ever since I tried this,” Phil chuckled.

“Yeah you’re right,” Dan smiled, ignoring how the butterflies were rioting in his stomach.

Being with Phil like this felt so different than being with him in the office. For one, Dan wasn’t naked. Phil didn’t have the dominant aura about him that he has in the office. And Phil never wore glasses at work, so this was the first time Dan saw him with them and he never thought it possible for Phil to look any better than he usually does already. Plus, they’ve only ever had one proper conversation that didn’t involve sex before, during that one lunch time. So this still felt new and weird to Dan. But it was a good weird.

Dan looked up and saw the barista smiling fondly at him and Phil from the counter. She seemed happy that Phil finally had company here. Dan wondered how many times she’d made a caramel macchiato for Phil, how many weekends she’d observed Phil sitting here alone. He wondered how many times he’d stopped by this place and inhaled the scent of coffee, only to walk past without realising that Phil was inside.

It was all getting a bit too much for Dan. He just wanted to take a walk to get his mind off of Phil and yet here he ended up with Phil right in front of him.

“Well I should uh…” Dan mumbled as he tried to get up, “don’t wanna bother you, I already do that enough when you’re actually at work.”

“You’re no bother, Dan! You can sit here, I don’t mind. In fact I’d love the company, it’ll be just like at the office. Without the, yknow,” Phil winked as he ended his sentence.

Dan knew he wasn’t working at the moment, but he found himself sitting back down anyway. He denied his mind telling him that he’d do anything Phil asked of him even without any pay.

“If you’re sure,” he said, to which Phil insisted that he’s sure.

Dan sat back and sipped on his coffee for a bit while Phil’s attention went back to his laptop.

“How long do you usually stay here?” He asked after a while.

“Depends on how much I have to do,” Phil replied, “I usually come here in the morning and go home at like 4 or 5.”

Dan thought his own life was dull, but Phil definitely beat him at that. He didn’t voice that though.

“Do you not wanna do other things, though? Relax a little on your weekends,” he replied instead.

“Of course I wish I could,” Phil smiled a little sadly.

Dan bit his lip, no wonder Phil needs a personal assistant in his office. He made a mental note to give Phil an amazing blowjob that he definitely deserves tomorrow.

“What about you? Headed anywhere after this?” Phil asked.

Dan had thought of leaving as soon as he was done with his coffee, but he suddenly found that he couldn’t bear to leave Phil be lonely here.

“Nahh, not today. I can keep ya company,” he said, leaning back into his seat.

Phil smiled and thanked him, looking genuinely appreciative. Dan wanted to kill all the butterflies inside him.

Dan felt comfortable just sitting there scrolling through his phone, listening to the taps of Phil’s keyboard. It was just like a normal work day, except he had clothes on and people around them. It was rather surreal how calm he felt now that he finally had Phil in front of him, compared to earlier in the park and the day before when he only had Phil in his mind.

Dan still hadn’t forgotten the incident with the other colleague on Friday though, and he decided to stay until Phil was done so that he could finally ask him about it.

* * *

“I can’t do anymore today,” Phil lamented, sighing when he saw that it was only half past 3.

“Was I being distracting?” Dan asked, trying to be cheeky but also apologetic if he really was a distraction from Phil’s work.

“Maybe,” Phil smirked, “but it’s not you, I’m just tired today.”

Dan felt like he had to help Phil relax, but he wasn’t working. So he just nodded sympathetically, not really knowing how to answer Phil.

“I guess I’m gonna head back home now,” Phil said, rubbing his tired eyes.

Dan was disappointed that yet again he didn’t manage to ask about the Friday incident.

“You got any dinner plans?” he asked on a whim.

“I was just gonna order some takeaway maybe,” Phil considered.

“Would you wanna, uh, have dinner together maybe?” Dan asked in a rush, surprised that he actually had the guts to ask.

Phil stared at Dan in what seemed like surprise too. Dan started to regret asking, because why on earth would Phil want to spend even more time with him when he probably just wanted to go home and rest for whatever little time left of the weekend he had before having to see him again tomorr-

“Yeah sure,” Phil smiled a little.

“O-okay,” Dan blinked, honestly not expecting that answer.

“You got anywhere in mind?” Phil asked as he packed his stuff.

“Not really…” Dan mumbled.

All the places he frequented were probably far too low-class for someone like Phil, who doesn’t even step into Starbucks anymore.

“How about that takeaway you were thinking of?” Dan suggested in the end.

Dan wasn’t sure where the line was between them outside of work and whether going to his boss’s home would be crossing it. But he remembered that they had a lot of favourite games and shows in common, and if he regarded Phil as just a friend then it could possibly be a fun and chill Sunday night.

But when Phil didn’t answer, Dan regretted his suggestion again and started rambling.

“I know it’s weird to ask to go to your home sorry about that maybe we could go-”

“No no it’s not weird, I’d like that actually,” Phil interrupted, “we can catch up on the new Game Of Thrones too.”

* * *

Phil drove them to his home, and Dan never felt more inadequate. And he’d been naked in an office for a whole month now.

He just wasn’t used to such a high-class life - he’d never even owned a car before - and Phil’s car was so luxurious that he felt out of place. Phil’s home was a whole other matter, too. It was the penthouse apartment in a building about a half hour ride from the coffeeshop.

Dan marvelled at the interior of Phil’s home. It had a minimalistic interior design, and glass walls similar to the office. It looked so clean, as if it was barely lived in.

But as Dan stepped further in and observed more, he realised that beyond the sleek design of the home, Phil’s endearing personality shone through in unexpected ways. There were googly eyes stickers on the switches, and a whole shelf of dvds, video games and even board games stacked up next to the television. Random knick-knacks like a dog bookend, a spiderman on the cord of the blinds and a dinosaur lamp all stood out and yet fit perfectly with the overall design of the home somehow. Dan thought about how this would’ve been the way he’d decorate his own place too if he had the money.

“Welcome to my home,” Phil proclaimed, “Make yourself comfortable, I’ll order some Chinese.”

Dan awkwardly sat by the edge of the couch, almost feeling like he had to take his clothes off or something. He realised he’d never been clothed when alone in a room with Phil besides his interview.

Phil set his tv up and they started watching the new season of Game of Thrones while waiting for their food. Dan kept stealing glances over at Phil, feeling a little anxious. But Phil didn’t seem awkward or tense, so Dan tried to just see the situation as being over at a friend’s, not at a crush’s or a  _boss’s_  home.

When dinner arrived and the show went on, Dan started relaxing more. He actually had fun; he’d never watched his favourite show with someone else before, and it was fun to be able to discuss the show with someone who was equally invested in it.

The takeaway was amazing, too, unlike any of the cheap ones Dan was used to. He finished his noodles so quickly that Phil joked that he should’ve ordered more. Dan just blushed, he hadn’t realised how hungry he was until he started eating, especially since he missed lunch to accompany Phil.

It soon got harder for Dan to concentrate on the show with Phil sitting so close to him. They had both ended up slouching, and their shoulders were almost brushing each other’s. Phil didn’t seem bothered, but Dan swore he could feel sparks every time his shoulder lightly bumped against him, or when his knee brushed his thigh.

“Is that a Starbucks cup on the table?!” Phil exclaimed.

Dan turned to him in shock at his sudden reaction, but was even more surprised when he realised just how close he was to Phil. The last time he could feel Phil’s breath on his face, they almost kissed. But of course Phil didn’t that time.

But Phil didn’t move away this time. Dan could see the twinkle of excitement in Phil’s eyes.

“Shame they don’t know what good caramel macchiato is,” Phil joked instead.

“Didn’t know they even had Starbucks,” Dan joked back, but he was rather distracted by the pretty lips right in front of him, so close to his.

Dan noticed that Phil followed his line of sight before he promptly turned back to the tv. Dan didn’t know if he’d imagined Phil stilling before turning away, but he did know that he should’ve seen that coming. Still, he felt a pang of disappointment. Once again he had to remind himself that Phil didn’t want any of that romantic shit. Phil just wanted company and a good fuck. He wasn’t paying Dan to be his boyfriend, damn it. In fact he wasn’t even paying Dan on weekends, it was his own damn fault for suggesting dinner together.

“Can’t believe they left that in,” Phil chuckled, sitting up straight with his eyes trained on the tv.

They didn’t really speak after that, Phil concentrated on the show and Dan let his mind wander. Dan didn’t pay attention to the show at all, instead wondering how the hell he got into this situation. His life was pathetic as it is without having an unrequited crush being added into the mix, thanks. And a crush on his  _boss_  of all people. Whom he worked for as a personal slut. What is his life.

Dan wondered if in another universe, they’d find each other in different circumstances and they’d be good friends. Or more than friends. But he’d take their current unusual arrangement over nothing.

When the episode was over, Phil spoke up first. “Thanks for accompanying me today, even though you’re not being paid.”

“It’s alright, I would’ve been alone anyways. It was fun hanging out,” Dan said honestly.

“I’m glad you enjoyed dinner, and didn’t think this would be weird or whatever,” Phil smiled.

“Guess I’ll see you tomorrow?” he asked when Dan didn’t continue the conversation.

“Does the office think it’s weird though?” Dan asked belatedly, surprising himself again with the way he was running his mouth today.

Phil looked puzzled for about two seconds before masking on a neutral expression.

“No I’ve told you, you weren’t the first,” Phil answered slowly, careful with his words.

“Then why was that guy so worked up on Friday?” once Dan started with his questions, he wouldn’t stop.

Phil sighed a little. He’d hoped that Dan would forget that little incident by now.

“Don’t worry about anything, okay? You only work for me, you don’t have to concern yourself over others outside our room.”

“I just wanna know why he seemed upset that you got a new…assistant,” Dan pressed. It had been eating him up all weekend, and he took advantage of this moment to say what he wanted to while he wasn’t serving Phil.

“Because clearly the first one didn’t work out so he was just concerned that things might repeat again,” Phil replied thinly, not liking how Dan was prodding on this topic.

Dan’s face softened. Whatever the first assistant did wrong, he wanted to be sure that he won’t do it. He wouldn’t want to repeat those mistakes for Phil’s sake. He just needed to know what the mistakes were in the first place, but he could sense that Phil was almost done having this conversation already.

“I’ll make sure that this will work out for however long you need me,” he assured Phil.

Phil’s guarded stance seemed to wilt a little at that. He smiled a small, sad smile, as if he was touched that Dan was so willing to stay.

“I promise things won’t repeat if I know what…things…I should avoid doing,” Dan worded his sentence carefully, leaving it open for Phil to discuss instead of forcefully asking him about his former assistant.

“Just keep up with what you’ve been doing and how you’ve been behaving and you’re fine. You’re a good boy,” Phil answered.

Dan melted at the last sentence. He blushed as he murmured out a thanks. He was so easy to distract, but he wanted Phil to stay on topic.

“But why didn’t the first one work out?” Dan asked again, more direct this time.

Phil was keeping his expression well guarded, Dan wasn’t sure if he was sad or angry. But his answer just confused Dan even more.

“Things don’t always go as planned, I guess, and we just have to learn that that’s life. Accept it and move on.”

“Did he hurt you? Is that why your colleague was so concerned?”

“There are some things you don’t need to know and you just have to accept that, Daniel,” Phil snapped.

Dan sat back a little, not expecting Phil to raise his voice or show his dominant side.

“I’m sorry, Sir,” he uttered, already feeling ready to accept a punishment for speaking out of line even though he knew he wasn’t working.

Phil sighed again. Half of him did feel like just going full Dom to stop this conversation, and he could see that Dan was already starting to be submissive just from his tiny outburst. But he can’t do that. He can’t take advantage of Dan like that when he wasn’t working for him right now.

“I already told you, you don’t have to call me that today.”

Dan just bit his lip and stared at his hands, trying to think of how not to end the good day on a bad note, but coming up with nothing.

“Look, I’m sorry Dan. But like I said, you don’t have to concern yourself with things that don’t concern you, alright? If there is a need for you to know something, I’d tell you. Just do what you gotta do, which is what I tell you to. And I’m telling you to stop worrying over nothing.”

It didn’t seem like nothing to Dan, and he still wasn’t convinced that Phil’s conversation with his colleague on Friday didn’t concern him. But he didn’t want to frustrate Phil any further, so he decided that it was enough for tonight and nodded in agreement.

“Okay. Let’s just forget this, I didn’t mean to ruin the fun we’ve been having,” Dan said guiltily.

“It’s alright, I understand. I did have fun anyway, it was nice hanging out with you as a pal rather than an assistant,” Phil chuckled a little.

“I could always be in your office as a pal,” Dan joked, trying to lift the mood back up.

“Nahh I still want my good boy in the office,” Phil smirked, getting up.

Dan tried his best not to look too flustered by that statement as he followed Phil to the door.

“Goodnight, and don’t be late tomorrow!” Phil warned with a cheeky smile before closing the door behind Dan.

Dan stared at the door for a while, in disbelief that he’d just spent almost the entire day with Phil. He’d like to call it a date, except his feelings were definitely not being reciprocated. Plus he almost ruined it towards the end. His curiosity about Phil’s past assistant only increased after that conversation, but he just had to listen to Phil and accept that he didn’t have to know everything.

He mulled over the day’s events as he headed home. Other than that conversation and the almost-kiss  _again_ , he did have fun with Phil. Even the moments when they weren’t talking and were just being comfortable in each other’s presence. Sure it wasn’t a cute picnic with cake and sitting in each other’s laps giggling about nothing, but it was still better than spending the day alone doing nothing but thinking about him.

Dan hated to admit it and he’d been in denial for a while, but he was well and truly falling for his boss.

**Notes for the Chapter:**

> tbh wanted to have smut in this chapter but idk what happened I somehow ended up with this. I hope you liked it, I know non-smut isn’t my forte lol so I was scared they’ll seem out of character compared to the previous chapters but I tried :x


	6. Chapter 6

**Notes for the Chapter:**

> almost exactly 3 months since the last update, good job me :| sorry to have kept yall waiting but I was writing this halfway when irl d&p came out, which was so surreal and overwhelming that I had to take a lil break from writing phanfic, I hope you guys understand <3

After Dan left, Phil couldn’t stop thinking about the conversation they had. He should’ve known it was a bad idea to let the boy into his home, but he couldn’t help it. He can’t believe history was almost repeating itself. All he had to do was maintain his distance, keep the boy aware of the line between them. Boss and assistant, nothing more. Don’t cross the line, and everything will be fine. And yet here he was.

Phil cursed himself as he slumped back onto the couch. He could tell that Dan liked him. Why else would anyone even want to spend their precious weekend with their boss the entire day? But he wouldn’t blame the boy. And to make matters worse, Phil was starting to grow very fond of Dan too. It wasn’t easy avoiding his pretty lips earlier. He wanted nothing more than to kiss Dan, to taste him, to learn the way his lips felt against his own.

But that was exactly what started the downfall of his relationship with his previous assistant, and he wasn’t going to let it happen again. He absolutely did not want to lose Dan the same way.

Perhaps Frank was right, Phil thought. His colleague was just looking out for him, not wanting him to be silly and fall for an assistant again, but Phil clearly hadn’t listened. Frank had all the right to be upset at him on Friday. But part of Phil had wanted to prove to his colleagues that he knew not to repeat mistakes, and he thought that having Dan would be a good idea to show them. God, Frank would be  _pissed_  if he ever found out that Phil had spent almost his entire Sunday with Dan. 

But Phil had enjoyed Dan’s company very much, even more so than when he sits naked all pretty in his office. He never had someone so willing to just accompany him even though he was busy doing work. He never had someone to watch his favourite show while eating his favourite takeaway food with before. Not even when he was in love with his previous assistant.

Phil thought about how well he and Dan actually clicked. He wondered if in another universe, they’d meet in a different way and be boyfriends. He entertained the thought only for a minute though, he couldn’t afford to lose an assistant again.

Phil sighed. Maybe he should just let Dan know about the past, maybe Dan would be better than him at staying within boundaries. He didn’t want to lead him on if they continue this way. But he was afraid that Dan might leave entirely if he were to tell him. 

As he started clearing away the takeaway boxes, he decided that instead of talking about the past, he’d just have to show Dan the boundaries even clearer.

* * *

 

The next day, Phil stepped into the office to be greeted with the usual sight of Dan sat on the rug and the usual scent of coffee already made for him. Phil had somewhat expected Dan not to turn up after yesterday’s events, so he was actually pleasantly surprised. He didn’t show it, though.

“Good morning, Sir,” Dan spoke up, actually feeling good that he could finally call Phil Sir again after not being able to yesterday.

“Good morning, Daniel,” Phil answered, making a point not to look Dan’s way as he settled down in his seat.

Dan gulped, not sure if Phil was still upset at him for their conversation the previous night. Phil was usually warm and cheerful in the mornings, except that one time he was late. But now he seemed guarded, like last night.

Phil seemed intent on not even speaking to him. Which was strange because Phil always had some instructions for him before he started his work proper. So, Dan decided to go through with his plan from yesterday which was to give Phil a deserving blowjob before he started the day.

He crawled over and knelt by the side of Phil’s chair, doe eyes looking up at Phil before asking if he could blow him. To his surprise, Phil merely dismissed him.

“From now on, I want you to kneel and be still by that corner when you’re not needed. Only come to me when I ask you to, got it?” Phil asked, pointing to the far end of the room.

Dan was confused, because Phil had always allowed him to just be comfortable and do whatever he wants if he wasn’t needed. But it wasn’t his place to object to instructions.

“Is this punishment for pushing things yesterday, Sir?” he asked, albeit meekly.

“No,” Phil answered a bit more defensive than he’d intended, “I thought we agreed to forget that. I’m just setting some new rules for you,” Phil gave Dan a quick glance before turning his attention to the files on his desk.

As Dan crawled dejectedly to his newly designated corner, he concluded that this was  _definitely_  because of yesterday. Just as he got into position, Phil spoke up.

“Oh before that, go get the black buttplug and use it.”

Dan went to the drawer of toys, knowing exactly which one Phil was referring to. He started moving towards Phil but Phil stopped him and told him to get it in himself.

Dan was used to Phil preparing him and using the toys on him instead of doing it himself, but he just had to adhere to whatever Phil was saying right now. So, he decided to make the most of it and put on a good show for Phil. He prostrated on the rug, head down and ass in the air towards Phil. He slowly fingered himself, complete with moans and whimpers that he knew Phil liked.

After he finally inserted the plug and sat back up and turned to Phil, to his dismay, Phil wasn’t even looking at him.

Dan huffed as he crawled to his corner. What was the point of him being there if Phil didn’t even want to pay attention? He knelt up and faced the wall, wondering how long he’d have to stay like that. He couldn’t even see the time like this, and he knew he’d be bored to death before even an hour passes.

* * *

 

Dan wasn’t sure how much time passed but his knees were starting to ache. He wanted to turn around and look at Phil, but he didn’t want to disobey orders. He wanted to be as good as possible and not make any mistakes. Perhaps the previous assistant eventually got bored and even the money can’t cure boredom. Or perhaps he got so bored that he started disobeying orders a lot on purpose so Phil fired him. No, Dan can’t be like the previous assistant. So he continued kneeling like a good boy despite his knees aching.

Phil actually couldn’t stop staring at Dan’s ass while he tried to do work. The plug was a perfect touch. And Dan was being so good as well, he was barely fidgeting. Phil almost felt bad that he had to do this, but it was the only way he could think of how to keep the boundaries in check. 

Just then, there was a knock on Phil’s door. He instinctively looked at Dan, who was already looking back at him.

“Go,” Phil mouthed and pointed to the bathroom door.

“I’m good,” Dan responded in a moment of defiance. He remembered that Phil hadn’t minded if he wanted to stay when people came in. And he didn’t want to miss out on any conversation that could potentially involve him anymore.

“It’s an order,” Phil said firmly, face stern.

Dan faltered a bit. He contemplated disobeying Phil, but he really didn’t have it in him to be a naughty boy. He didn’t have much time either; the knocks on the door were getting louder and Phil was looking angrier by the second.

Eventually, he got up and ran into the bathroom, closing the door just in time for Phil’s colleague to barge in.

* * *

 

“You’re hiding him in there, aren’t you?” Frank asked, clearly unamused as he sat down in front of Phil’s desk.

Phil sighed. At least Frank wasn’t raising his voice like last time, so hopefully Dan couldn’t hear anything.

“Yeah okay I guess there’s no point lying to you anyway,” Phil mumbled.

“You know I’m just looking out for you, right?” Frank leaned forward in his seat, volume as low as Phil’s.

“Where is the old Frank who just wanted a piece of my assistant now?” Phil tried to joke even though he knew it won’t go over well.

“I don’t want you getting all hurt again, and I don’t want you hurting some kid’s feelings again.”

Frank was older than Phil, and although he knew that Frank was right most of the time, he didn’t like how sometimes it just felt like he was being scolded by his dad or something.

“I get it, Frank, but trust me I know what I’m doing this time,” Phil said.

“You sure you’re not falling for this kid now?”

“I’m not!” Phil whisper-shouted.

Frank didn’t look convinced, “Uhuh yeah, sure you aren’t. I would’ve received the complete financial plan from you if you weren’t distracted. I’ve known you too long to be fooled by you, Lester.”

“I’ll get it done by lunch, alright?!”

“Why can’t you just get a boyfriend the normal way,” Frank shook his head, “go on grindr if need be.”

“I’m  _not_  searching for a boyfriend. I just-”

“Then make sure he isn’t being led on. Or do I need to get in there and talk to him myself?”

“I  _am_  making sure of that. We have a contract and he’s being paid so. I’m not just using him and he knows what he’s gotten into,” Phil still tried defending himself.

Frank sighed as he got up.

“Well, if you need help you know I’m here for you. Just, don’t be stupid again.”

Frank immediately left the room, not giving Phil time to argue further. Phil knew that Frank was trying to be a good friend looking out for him, but he couldn’t help being more grumpy from that conversation.

Dan must’ve heard the door slam shut as he slowly came back out of the bathroom. Phil hoped that he hadn’t heard anything at all.

Dan could tell that Phil was frustrated, it seemed like his mood went from bad to worse. Just like on Friday, he felt like he should help his boss relax. It was his job here anyway. But he wasn’t sure if it would be a good idea now after Phil set those new rules.

He couldn’t make out any words from the conversation today, which frustrated him a little, but the voice he heard sounded like the one from Friday. He wondered what it was about the guy that always put Phil in a weird mood.

Phil felt Dan’s eyes on him, so he pretended to be busy until Dan gave up and moved to his corner. When Dan’s back was facing him again, he relaxed and sighed.

He had no idea what to do after the conversation with Frank. Dan was such a good sub, perhaps too good for him. He didn’t even try to object to the sudden change in rules. Now Phil wasn’t sure if the rules would even help at all. Part of him wanted Dan to just lash out on him, like his old assistant used to.

His old sub would’ve totally disagreed with the idea of having corner time, would’ve done the opposite of what Dan was doing and instead would do anything to push Phil’s buttons, even after Phil punished him. Phil shook his head slightly at the memory, wondering why he had even put up with that. He did love a bratty sub at the time, but Dan made him realise how beautiful it was to have a wholly willing sub too.

It was about an hour to lunch, so Phil decided to ignore his situation with Dan for now to finish up the work he owed Frank so that Frank wouldn’t come for him in the afternoon. He could try to talk to Dan during lunch.

* * *

 

“Dan.”

Dan was startled out of his daydream. He looked over his shoulder, uncertain if he was allowed to move out of his spot. He quickly stood up when Phil beckoned him over to the couches, his knees almost buckling.

Phil had ordered in for their lunch today. Dan cautiously sat at the opposite end of the couch. He still felt wary around this bad mood Phil.

Phil started eating, so Dan followed suit, but found it hard when the silence between them felt so tense. But he had no idea what to even say that could ease the tension, so he just tried to quickly finish his food.

Phil sighed suddenly, placing his bowl onto the table haphazardly.

“Dan,” Phil began, in a voice so solemn that it made Dan worry if he was in trouble or something.

Phil had no idea how to start the conversation, and Dan already looked like he’s terrified that he’d done something wrong. Why did he even pull this poor boy into this situation? It all suddenly seemed extremely silly to have a personal slut readily available for him at all times in his office.

“Could you put on your clothes?” Phil decided to say. Even though he loved seeing his boy nude, it just didn’t feel right for this conversation he was about to have.

“A-am I being fired?” Dan asked brokenly, and Phil can’t believe that tears were actually forming in Dan’s eyes.

“No,” Phil reassured quickly, “I just. Are you 100% sure you’re comfortable with all this?”

 _You’re like over a month late in asking this_ , Dan thought as his brows creased in confusion.

“Yeah, I mean I wouldn’t have signed the contract if I wasn’t,” Dan answered firmly, wondering why Phil was suddenly having doubts of his trust.

Something was clearly bothering Phil, but after what happened at his house, Dan didn’t want to overstep any boundaries by asking too much again. He was so curious but he hoped that Phil would trust him enough to open up to him without being prompted.

“I’m sorry, Dan,” Phil sighed, shaking his head, “I-I just. Wanna ask you something. Can you be completely honest with me?”

Dan was still confused as to why Phil didn’t seem to trust him suddenly. “Of course. You know that I’ve never been dishonest with you, right Sir?”

Phil didn’t answer Dan. He stalled for a bit, trying to phrase his question in his mind.

“There’s nothing more going on here, right?” Phil asked vaguely, gesturing between them.

“W-what do you mean?” Dan asked nervously, having a strong suspicion of exactly what Phil meant.

“You know that as a boss and employee we must maintain a professional relationship, so I just wanna make sure-”

“Oh yeah, I know that,” Dan quickly uttered, “yeah totally. And yeah nope, nothing more here. Totally professional only.”

“Okay good,” Phil leaned back into his seat a little.

Dan felt bad seeing how Phil relaxed. Now he can’t say that he’s never been dishonest with Phil anymore.

“...Why’d you ask? Are you feeling like there is?” Dan asked to distract from his moment of faltering.

“N-no! I just. Want to confirm, is all,” it was Phil’s turn to falter.

 _So much for asking for complete honesty when you can’t give him that yourself_ , Phil thought.

Phil cleared his throat. “Yeah, which is why I set those new rules today. To have clearer boundaries between us. Just to be sure so nothing more could come up, which we obviously can’t tolerate. Yeah. Just wanted to explain to you why we’re gonna have these new rules.”

“Okay,” Dan said passively.

“Good,” Phil replied anyway even though he was exasperated by Dan’s blank expression. He picked his bowl back up and the conversation ended there.

* * *

 

Dan spent the rest of the day in his corner. It was the first day since he started working there that Phil didn’t even play with him once. He had a lot of time to mull over the conversation they had at lunch, and he honestly felt like he was in deep shit.

Perhaps he was more transparent than he thought, and he felt embarrassed thinking of how Phil most probably knew that he was falling for him. It was a good call on Phil’s part then, to set new boundaries. Dan thought he could’ve silently dealt with the crush, but of course he didn’t want want to make Phil uncomfortable and ruin their workplace relationship. He was glad that Phil didn’t just fire him, even if he could tell that Dan was lying to him earlier.

He tried not to read too much into how Phil answered him the exact way he answered Phil. Was Phil really being honest or did he also lie just like Dan did? What if Phil was also starting to fall for Dan and so he quickly set new rules to make sure he wouldn’t? Dan felt his heart swell thinking about Phil actually liking him back, but he didn’t want to entertain those thoughts for long. They wouldn’t make things any better.

The more he thought about their conversation during lunch, the more questions he had. But he was sure that part of why Phil was doing this was because he’d been too nosy the day before, and he didn’t want to overstep by asking too much again. He so badly wanted to tell Phil that he won’t cross the line anymore, that he can be good and maintain a totally professional relationship - whatever that meant for a personal slut - without having these new rules that he honestly didn’t like at all.

The problem was. Although Dan absolutely did not want to get fired over being unable to control his feelings, he was fairly certain that even this change can’t stop him from falling for his boss. He was definitely in deep shit.

* * *

 

Phil could concentrate on work even less now than when he often played with Dan. The new rules weren’t helping him at all. He kept looking at Dan, who amazingly stayed still almost throughout the entire day. His eyes scanned the boy’s taut shoulders, the little freckles speckling his shoulder blades, the dimples above his bum. They way he’s gripping his arms behind his back even though Phil hadn’t made him do that. Such a good boy. He wanted to pull the plug out and fuck him hard against the wall.

But he also kept thinking about the conversation they had over lunch, and how he wasn’t sure if this could help Dan not to be led on.

Not that Dan was being led on since his feelings were reciprocated, even if he didn’t know. Which was a whole other matter that Phil wasn’t prepared to think about.

But he’d already tried to make clear that he wanted to have only a professional relationship between them, and he shouldn’t take back his words. He wondered how Dan was taking this all so well. He literally agreed to have these rules without even questioning Phil the slightest, which honestly took Phil by surprise.

Maybe Phil was just overthinking and all this was unnecessary. Or maybe Dan felt that this change was helpful, and things could work out with no feelings attached in the end.

Phil sighed as he continued staring at his boy’s ass across the room. He thought about how adamant Dan was that there was nothing more going on. He didn’t know whether to believe the boy, because his actions sure showed otherwise. Not that he had a right to get mad, since he also lied to Dan about his own feelings. Although he really hoped that Dan didn’t pick up that he’d lied.

The image of Dan looking distressed thinking that he was being fired also stuck in Phil’s mind. At least one thing’s for sure - Phil need not worry about his assistant wanting to leave him like last time. As long as he doesn’t mess things up now.

 

Phil quickly shook himself out of his daydream of being with Dan and focused on his work for the rest of the day. If he wanted Dan to lose the feelings, he had to as well. So maybe trying to show the boundaries clearer this way would work out after all.

At the end of the day, Dan was instructed to remove the buttplug without being played with even a little. After over a month, this was his first day there that he hadn’t enjoyed at all.

**Notes for the Chapter:**

> I hope expectations aren't too high for this fic (tbh idk how this became one of the favourites lol). Part of why I took a while to come back even after the feeling of omgwtfhshshskjs towards d&p’s coming out died down was because I literally have no clear plan for where this fic is going, which is a huge flaw of mine as a writer who just can’t seem to plan the entire story first instead of taking things one chapter at a time oops :x
> 
> butttt I hope this update was okay and thank you for still reading and being patient even as I tend to disappear for months at a time <3


	7. Chapter 7

And so that was how they continued for the rest of the week. Dan stayed in his corner, not having the guts to tell Phil that he actually hated it. Phil barely played with him; he used the vibrating buttplug once, but that was all the fun Dan got. He really would rather be edged by the plug and denied release again than doze off by the wall. The only times he was tasked with things to do were when Phil asked him to fetch him things from the other end of the room, or make him a drink.

Dan was bored out of his mind, and it was actually making him start to dread going to work. He’d take anything by this point, even the most hardcore shit he’s ever done would be better than doing nothing all day. Even their lunchtimes were awkward, and Dan felt as if Phil didn’t want him there anymore, wasn’t interested in him anymore. Deep down he knew that it was just Phil trying to maintain a professional relationship and not get too carried away, but he really missed the attention he used to get from Phil.

Phil, on the other hand, was losing his mind. The more he didn’t allow himself to play with Dan, the more he just craved for the boy. What a fool he was for thinking that this arrangement could dissipate his feelings for the boy. But he thought that at least Dan was benefiting from this idea, judging by the way he still seemed eager to follow his orders and wasn’t averse to them. So he did it for his boy’s sake.

* * *

 

Phil huffed as he slammed his office door shut. The meeting he just had didn’t go well in his favour, and angry was an understatement of how he was feeling.

He began walking towards his desk when he caught sight of his boy sat on his rug.

“What are you doing out of your corner?” he asked, voice menacing without meaning it to be.

Dan had meant to talk to his boss about their new arrangement for a while now, but never mustered up the courage until Phil left for his meeting. He’d spent the whole 2 hours that Phil was gone planning the entire conversation in his head, making sure he’d remember his points and hyping himself up so he wouldn’t change his mind about doing it. He’d moved from the corner to wait for Phil at the usual spot he used to laze around on before Phil set the new rules.

However, he hadn’t taken into account the possibility that Phil’s meeting could go bad and turn his mood sour. Dan looked up at Phil in shock, wanting to answer his question but unable to find his voice.

“I-I…” Dan stuttered, instinctively leaning back when Phil started walking towards him. A boss in a bad mood still intimidated him.

If it was any other time, Phil would’ve been intrigued by Dan’s sudden change in behaviour. But in this moment, he was already angry and wanted some downtime by himself to cool off, and Dan breaking a rule just worsened his temper. As if his body went on autopilot, Phil stepped close to his boy and towered over him. Without a second thought, he proceeded to cool off the way he used to.

He unbuttoned his trousers hastily, not missing the way Dan’s eyes widened, the way his adam’s apple bobbed as he gulped.

“Open,” Phil commanded in a gruff voice, and Dan didn’t need to be told twice.

If Dan had known that being angry would make Phil use him then maybe he would’ve tried making him angry sooner. He eagerly knelt up and opened his mouth. Phil was barely hard, but he could change that real quick.

Phil had no desire to go slow and sweet. He grabbed a fistful of Dan’s hair, tugging at it as he pushed the boy’s head down onto him. He groaned as his dick was engulfed in the warm, wet mouth, feeling himself get aroused.

Dan licked around Phil’s cock, feeling it harden in his mouth. He’d missed the weight of it on his tongue, the taste of his boss and his musky smell as he buried his nose in Phil’s crotch.

Phil didn’t loosen his grip on Dan’s hair, instead holding him in place. As he grew harder, he began thrusting his hips. Dan was blinking up at him with his damn doe eyes, and Phil could feel the fire in him turn from rage to lust.

Dan’s hand moved up to fondle Phil’s balls, but Phil swatted them away.

“Hands behind your back,” Phil growled, and Dan had to stifle a whimper as he did as he was told.

Dan was absolutely loving the rough treatment, and he felt his own dick grow hard as Phil kept thrusting relentlessly into his mouth.

Phil pulled out for a moment to let Dan gasp for air. He couldn’t resist smacking his dick against his boy’s rose coloured cheeks. Dan looked debauched, his mouth open, lips slick with saliva, and eyelashes fluttering every time he was slapped with Phil’s dick. Phil couldn’t believe he’d been refraining himself from this pleasure, and for what?

He pushed back into Dan’s mouth, feeling his tip hit the back of Dan’s throat. Dan barely gagged, and Phil was glad that his training hadn’t gone to waste while he wasn’t being used.

Dan swallowed around Phil, and Phil couldn’t help the moan he let out. He pushed himself impossibly further into Dan’s mouth, relishing in the boy’s choked whimpers as he held his head in place.

Phil’s thrusts got rougher as his orgasm drew closer. Dan relaxed his jaw and let his boss use him, unable to do much besides just taking whatever was being done to him. His grasp onto his forearms was tight, nails digging into his skin.

Phil groaned as he reached his climax, and he felt Dan swallow as he came in his mouth. He shuddered in pleasure and only pulled out when he was done coming.

Dan panted and licked his lips, looking up to see Phil gazing back down at him. Phil was smoothing the hair he’d been pulling, and Dan felt bashful suddenly. He nosed at Phil’s softening dick, and gave a shy smile. He was just happy to be doing what he was here for in the first place, and by the looks of it, Phil was too.

But all too soon, the soft moment was over as quickly Phil tucked himself back into his pants and went back to his desk. Dan was left kneeling there half hard and confused. He almost forgot how he ended up out of his corner, but when he remembered his little monologue, he wasn’t sure if Phil would want to listen right now.

Phil seemed to remember that Dan was for some reason out of his corner only after he sat down. The boy was sitting on his heels on the rug, hands still loosely gripped together behind his back. He was stealing glances over at Phil, probably thinking that Phil didn’t notice. He seemed like he wanted to say something but was unsure if he could.

Phil mentally smacked himself for acting on impulse like that after days of having things under control. But at the same time, this was what he’d hired a personal assistant for anyway, so he had nothing to feel guilty about, right? He could do this, as long as he didn’t let emotions come into play.

Dan bit his lip, still tasting his boss on his tongue. Should he speak up now? He couldn’t tell if his boss had fully calmed down yet. But just as he opened his mouth to say something, his boss beat him to it.

“Get back to your corner,” Phil spoke, voice low and tone warning Dan that he shouldn’t try crossing him.

Dan sighed inaudibly, dropping his hands to the rug to crawl back to his place. But as he looked at the wall he’d been stuck at for days, he felt that he just can’t do it anymore.

“Sir I-”

“Why are you being disobedient?” Phil snapped, looking up from his paperwork.

Dan was honestly a bit taken aback, he’d never seen his boss this angry. He had half a mind to explain himself, but decided it was best to just do as his boss says. He apologised softly before quickly going back to the wall.

He really didn’t have it in him to go against his boss’s orders.

* * *

 

Phil leaned back in his seat as he tried to cool down. He felt bad for lashing his anger out at Dan, who’d been nothing but a good boy the entire week. Except for some reason being out of his corner when he returned from the dreadful meeting. He looked at the clock and realised it was almost lunch, so he quickly ordered some food.

His mind wandered to his past assistant, who would’ve spoken his mind despite Phil’s orders. He figured that perhaps Dan had wanted to explain his behaviour, but he was too good a boy to speak out of line. He’d have to ask him about it at lunch.

* * *

 

“Dan,” Phil called over as he laid lunch on the table.

Dan could tell it was lunchtime, but he felt like he deserved more corner time or something. He’d spent the time between the blowjob and lunch just thinking over his actions and regretting breaking the rules. He shouldn’t have even tried doing what he’d planned to. He also wondered if his boss would’ve fucked his mouth after his meeting if he wasn’t sat at the rug. Even though he’d enjoyed finally getting some sex, he felt like he didn’t deserve the enjoyment after being disobedient.

He got up anyway, not wanting to piss Phil off further. He sat quietly and accepted his food.

“Care to explain what you were doing earlier?” Phil spoke up first.

Dan was glad that at least Phil didn’t sound angry anymore. He just sounded tired.

“I-I..” Dan began, wondering if he should still try bringing it up or just forget it. Phil seemed like he had a lot on his mind, and he didn’t want to add to that.

“It’s- I shouldn’t have moved out of the corner, Sir, I’m sorry. I don’t know what I was thinking,” Dan lied, looking down at his food.

Phil squinted at him in disbelief.

“I won’t punish you, I just want to know what’s on your mind. You looked like you were going to say something when I came in, I’m sorry I interrupted you like, uh, that. Shouldn’t have let my temper get the best of me. And just to clarify, I wasn’t angry at you.”

“It’s fine, I liked it,” Dan admitted before he could stop himself, making Phil smile cheekily.

“I-I mean like. I’m always here when you’re stressed. Happy to help you relax,” Dan babbled.

“I’m glad that you like doing your job,” Phil chuckled, ”anyway, back to what you wanted to talk about.”

Dan took in a deep breath. He forgot his planned monologue and his confidence to bring it up was barely there anymore. But ultimately, he knew that Phil was an understanding man and would regard his opinions seriously.

“I…I don’t like having to be in the corner all day, Sir,” Dan said softly, not daring to look Phil in the eyes.

Phil raised his eyebrows in surprise. He’d thought that Dan found the new arrangement good for them.

Dan saw that Phil was just looking at him waiting for an explanation, so he continued.

“I wanted to tell you when you got back from your meeting. But I know I shouldn’t have disobeyed the rules and I’m sorry, Sir, it was silly of me.”

“You don’t have to be sorry, I’m glad you’re telling me. You know it’s in the contract that we can always adjust limits and rules if you don’t feel comfortable doing them, right?”

Dan knew it, but still he felt like it wasn’t his place to demand changes.

“I guess… I just miss getting to do all the other things in that contract, and things like earlier,” he said sheepishly.

Phil poked at his food as he pondered on what to do.

“You know why I set those new rules?”

“To have clearer boundaries?” Dan answered, though he made it sound like a question. “Sir, with all due respect, I feel that the way we were before these new rules was already good enough.”

“Yes, but do you know why I felt like this was important to do?”

It’d honestly been on Dan’s mind but he didn’t dare run his mouth with questions ever since the conversation they had in Phil’s home. He didn’t know how to answer Phil now, either, but thankfully Phil wasn’t actually waiting for an answer.

“Because I was careless with my previous assistant.”

Dan was surprised that Phil brought it up, but he didn’t say anything in case Phil would change his mind about telling him the story he’d been dying to know.

“I let our feelings get the better of us, and before I was able to take control of things, it’d gone too messy. I hadn’t meant to fall for my assistant, and neither did he. There were stupid misunderstandings, and I should’ve seen it coming but-” Phil stopped abruptly and shook his head, sighing.

Dan was trying to piece the story together. Phil wasn’t giving much details, so his mind filled in those blanks with his own assumptions of what could’ve happened between Phil and the old assistant. He felt bad seeing how talking about this still bothered Phil.

“I know you told me that you don’t feel anything more, so I believe your word for it. I wanted to add the rules to take extra precaution, but if you feel like they aren’t necessary then we can go without them.”

Now Dan felt extra bad, but he can’t possibly tell Phil that he had lied and is indeed having feelings for him. He wasn’t sure what to even say, but Phil wasn’t done; he still had more to get off his chest.

“To be honest I wasn’t sure if I was overthinking things and overreacting with all the new rules and whatnot, but I’m glad you brought it up so I know now that we don’t actually have to do all that. I’m sorry, I just didn’t feel prepared to tell you more before,” Phil huffed a hollow laugh, “which is stupid. I should be over it by now.”

Phil finally looked at Dan properly then, and Dan blinked as he struggled to find words to say. He’d thought the reason for the new rules was purely because of him talking out of line in Phil’s home.

“I know,” Phil chuckled, “I’m blabbering. Sorry. But the thing with my first assistant - I just got scared that it might repeat. I don’t want you to regret working for me too, y’know?”

Dan tried to ignore the way his heart sank. His rational thoughts told him that there was no way Phil liked him back, but he still foolishly had hope. He understood better why Phil wanted a barrier between them now. Phil clearly was so affected by whatever happened with the previous guy that he really didn’t want it to happen with Dan again. He didn’t want to accidentally fall for Dan the way he did with his previous assistant. Dan ignored his crushed heart.

“But…if the feeling was mutual between you two, why didn’t it work out?” Dan dared himself to ask. Phil’s story was still so incomplete, and he barely understood the full picture.

Phil sighed, hoping that telling Dan the full story wouldn’t be a wrong move.

“Well…like I said, misunderstandings,” Phil said regretfully. 

“He was quite the opposite of you. He was bold, always wondering around the office and loving the attention, trying to be  _everyone’s_  personal assistant. And he was a good sub. He obviously loved the job, but after admitting our feelings he just. Became bratty? Like, to the point where he started deliberately ignoring some rules for the fun of it. I guess he felt like he could do whatever since he was dating the boss,” Phil paused with a hollow chuckle, the memories flooding back to him.

“I tolerated it until I couldn’t anymore. I’d given him some rough punishments that I regret. He took things too far but… I did too. So then he wanted to leave. But somehow we still loved each other? So it was tough for both of us,” Phil spoke quietly, feeling strange talking about it.

Dan couldn’t help wondering how Phil could even think of getting a new assistant after whatever he went through with the previous guy.

“I’m sorry you had to go through that, it sounded like you two had a real complicated thing going on,” Dan offered.

 _But I would be so good for you! I won’t ever be like that guy!_ Dan screamed in his mind.

“Yeah, but whatever. You’re different from him, so I don’t know what I was so paranoid about. It’s like I’m punishing you for things that happened in the past that you weren’t involved in,” Phil sighed.

“But I understand why you felt the rules are important. I know I said I didn’t like them but they’re necessary so I’d accept them, Sir,” Dan insisted.

“No, you see, this was why I didn’t want to talk about all of it. I didn’t want the past to affect and dictate how we do things now. I’ve missed playing with you too, I’m not gonna lie. And if we’re sure that things won’t repeat then there is no need for making you stay in that corner everyday,” Phil said with certainty.

Dan swallowed. He wasn’t so sure about that. Of course he wouldn’t misbehave like the previous guy, but having his feelings mixed up in their arrangement was already a repeat of the past. And if he kept silent about it then what if a different kind of misunderstanding happens?

But Phil seemed set on removing the rules already. Dan thought in amusement how miserable Phil had probably been, having to stare at his ass from the other end of the room everyday but refraining himself from playing with him.

“I’ll make sure nothing would go wrong. And I need your help for that to work. Just promise me you’ll tell me honestly about everything, like you did about this new rules, which I’m happy you’ve done,” Phil smiled in appreciation.

Dan couldn’t think of doing anything other than nod, “Yes Sir.”

* * *

 

Dan laid on the rug after lunch, happy to not be on his knees staring at the wall anymore. Phil glanced at him every so often. But they were both occupied with worries.

Dan didn’t want to admit his feelings to Phil, because what if Phil thought that things would repeat and it won’t be worth dealing with again, so he just fired Dan instead? No, Dan absolutely cannot say anything.

Phil felt worse after the conversation. He kept demanding honesty from his boy but he couldn’t admit to himself, let alone the boy, that he was falling for him. And that he was terrified of making any mistake that could lead to Dan leaving him. He didn’t know if coming clean about it would make things easier, or scare Dan away.

Technically, Phil could tell that Dan was different from his previous experience. But then again, he never knew that his old assistant could end up so different. He looked back up at Dan and saw him gazing out the window. He sighed, and reminded himself to forget the past and just live in the moment.

“C’mere, Dan,” he startled the boy out of his daydream, “I think you need a cute plug up your ass.”

**Notes for the Chapter:**

> yay finally some sex again lol. anyway idk if it’s because I’ve been working on this update so much that I’m beginning to hate it and feel like it’s similar to the previous chapter aaa sorry but idw to restart and keep yall waiting so here you gooo I promise things will change up in coming updates ><


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